The Diary of a Love Torn Demon
by Daddy's LiL HeartBreaker
Summary: Ruby has known the Salvatores all of her demonic life and has known the Winchesters for three years. When both sides of her life collide, which side will she choose? The vamp who brings out her wild side or the hunter that brings out the good in her?
1. Chapter 1

**Author's Note: **Okay so this right here is Becks Rylynn's fault because she's the one that got me hooked on Damon/Ruby, Team Evil as she likes to call them, with her amazing one shots. Everyone should totally check out her stories though. They are so freaking amazing. This is my first time writing in the Vampire Diaries verse so I apologize if it sucks lol. Oh and _Italics _will be diary entries.

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter One:

It was for his own good. That was what Damon Salvatore had been told by his brother Stefan after he had woken up to find his signature ring missing from his finger. Without that ring, Damon couldn't go out into the sun. You'd think Stefan would of learned his lesson because the last time he stole Damon's ring, Damon had turned naive little Vicki Donovan into a vampire out of sheer boredom. Granted he could just wait until nightfall to have fun this time, but the whole daylight savings thing kind of screwed that up considering the sun was out for longer periods of time during this part of the year. Of course it wasn't long before boredom caught up to Damon Salvatore and he found himself sticking his hand out in front of one of the living room windows letting the sliver of sunlight peeking through graze his porcelain skin. He watched the smoke float up from the back of his hand for a moment before he moved out of the sun's way.

"I wouldn't do that if I were you. Might lose a hand or even more." Her voice drifted melodically through the old fashioned living room though he already knew she was there before she had even spoken a word.

A genuine smile appeared on his face slowly as he turned around only to see the blonde beauty leaning in the doorway casually, "Well well, if it isn't my favorite blonde. Now to what do I owe this pleasure?"

"Oh I was in town and thought I'd stop by to see my favorite vampy. Where is Stefan anyway?" She remarked with a playful smirk as she gazed over at the blue eyed vampire.

Damon chuckled softly and then appeared before her in the blink of an eye, "Very funny, Rubes. We both know full well that you and my brother can't stand each other. Besides, last time I saw you, Hunter boy was screwing your brains out."

"Don't call him that, Damon, he has a name. It's Dean Winchester and he happens to have a brother who is also a hunter. Keep it up and I could invite them over here." Ruby stared into his crystal blue eyes as her own blue eyes flickered to black for a moment before returning to their normal blue shade.

His porcelain face grew serious as he stared at her and then his lips twisted into an amused smirk, "Oh how cute! A demon being protective of two hunters. So how long before they try to kill you?"

"I don't know. I'm protective of two vampires also. How long before one of them kills me, vampy?" She retorted and scoffed softly as she pushed past him into the room.

Damon's features softened and he smiled as he watched her walk further into the room, "We'd never kill you, Ruby. You know that. Life wouldn't be nearly as fun without you."

"Yeah yeah. So what are you doing here anyway instead of out and about causing trouble?" The blonde demon questioned as she sat down comfortably on the couch.

He wiggled his bare porcelain fingers at her and poured himself a glass of scotch, "Brother dearest stole my ring. He's trying to housebreak me, but we both know it won't work."

"Again? Seriously? I say he shove him in the sun to make sure he doesn't sparkle. He is such a buzz kill." She rolled her blue eyes and snatched the glass out of his hand as he sat down beside her.

Damon watched her take a sip of his drink completely enthralled for a moment as her pink tongue darted out and then he snapped out of it taking his drink back, "Hey, get your own. Sparkle? Seriously? Oh god, you read those lame ass Twilight books didn't you? I threw it in the fire once I saw the word sparkle."

"No I didn't. I saw one of the movies though. It put me right to sleep." She shrugged her shoulders and snatched the drink back as he was mid sip.

He glared at her and she simply laughed as she downed the rest of the scotch. Ruby set the empty glass down on the antique wooden coffee table and squealed lightly as Damon grabbed her. They tumbled around before she found herself pinned beneath Damon on the couch with her hands held above her head. He stared into her eyes for a moment as his lips twisted into a rather seductive smirk and then he tilted his head running his tongue along the length of the side of her neck teasingly. His fangs appeared and he grazed them lightly against her skin only to retract them a moment later.

Damon stared down at Ruby and smiled softly, "Hello Stefan. Returning my ring, I hope?"

"Let her go, Damon. How did you even get her here anyway?" Stefan stood in the entryway of the living room with Elena by his side and all they could see of Ruby was her blonde hair.

Elena, however, glared at Damon convinced that the blonde was her good friend that she had previously warned the vampire to stay away from, "Damon, I thought I told you to stay away from her."

"God, a girl can't even get properly laid around here. I knew I should of just stayed with my hunters." She remarked to the obvious amusement of Damon as he let go of her hands allowing her to sit up.

"Ruby?" The younger Salvatore hadn't expected to see her here and knew he would have to do major damage control.

Unfortunately for Elena, the blonde demon looked in her and Stefan's direction upon hearing the younger Salvatore say her name. The appearance of the brunette by Stefan's side took Ruby by complete surprise as she hadn't expected to see her, but then again Ruby did automatically assume that Elena was someone else. Upon seeing the brunette, Ruby's bright blue eyes shifted into pure black pools of anger. The blonde took a running start for the brunette, but luckily for Elena, the Salvatore brothers proved to be too fast for Ruby. Damon held the blonde who's body was writhing in anger while Stefan blocked his girlfriend from the blonde's view.

Damon sighed and kissed Ruby's head as he carried her back over to the couch, "She's not Katherine. Trust me, we've checked. She is definitely not Katherine."

"Her name is Elena Gilbert and she's my girlfriend. Elena, this is Ruby, an old family friend." Stefan introduced the girls as he tried to calm the air between them.

"Hey! Who are you calling old, Vampy?" She chucked the empty glass at his head only to frown when he caught it in his hand effortlessly.

Elena clung to Stefan's right arm as she peered over at Ruby, "Her eyes are completely black. I've never seen anything like that before. Is she a vampire too?"

"Nope. Guess again, princess. I'm a demon." Her eyes flickered returning to their normal bright blue state as her lips twisted into an amused smirk.

The horrified look on Elena's face said it all and Stefan threw the stolen ring in Damon's direction before following Elena outside. Damon caught the ring effortlessly and slid it back onto his finger. He extended his hand to the denim clad blonde and she smirked before he whisked them both upstairs to his room in the blink of an eye.

_Dear Diary,_

_I arrived in Mystic Falls today and went over to the Salvatore boarding house. Damon and Stefan are still the same as they were the last time that I saw them. What is it with me and brothers? If it's not a pair of hunters, it's a pair of vampires. Speaking of Stefan, that little girlfriend of his is the spitting image of that damn Katherine Pierce. She isn't Kitty Kat though so I guess we can all be at least grateful for that. Alright, confession time, I slept with a vampire. Not just any vampire either. I slept with Damon fucking Salvatore. Yeah, I know, not surprising considering it is me after all, but it is the truth. I'm not staying long though. God forbid the Winchesters found out about Mystic Falls. They would stake first and ask questions later. Well, Dean would anyway. Ugh, I got to go for now. Stefan wants to have a little chat with me. Yeah freaking right. He probably just wants to warn me to not scare his pretty little girlfriend. Whatever!_

_Ciao Bitch,_

_Ruby xx  
_


	2. Chapter 2

**Author's Note: **Okay so this right here is Becks Rylynn's fault because she's the one that got me hooked on Damon/Ruby, Team Evil as she likes to call them, with her amazing one shots. Everyone should totally check out her stories though. They are so freaking amazing. This is my first time writing in the Vampire Diaries verse so I apologize if it sucks lol. Oh and _Italics _will be diary entries.

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Two:

"So how long were you planning on staying here in Mystic Falls, Ruby?" Stefan questioned the slender blonde as he watched her pour scotch into a glass.

"Why? Scared I'm going to attack the princess again? Relax Steffy, I won't hurt her. What fun would that be, anyway?" She remarked taking a sip of her scotch.

"I know how you and Damon are when you're together. I think it might be best if you cut this visit short." He suggested with a stoic expression upon his chiseled face.

"Really and who asked you, Steffy? Fine, if you must know, I wasn't planning on staying long anyway. I have other important matters to attend to, you know." Ruby's lips twisted into a smirk as she looked over at her old friend.

"You were never this bad before, Ruby. What happened to the girl I knew?" Stefan questioned appearing right in front of her in the blink of an eye and brushed away a lock of her soft blonde hair.

"The girl you knew? Stefan, you never knew me. Sure, we've been friends all these years, but you never really knew me. Damon was the one who knew me. He knew me better than anyone." She downed the rest of the scotch in one shot and set the glass back down on the wet bar.

Truth be told, Ruby had always been closer to Damon than she ever was with Stefan. Ruby always did feel like she could tell Damon anything which she often did. It had been Ruby that had discovered the truth about that dreadful Katherine Pierce, but it had been too late. Stefan had been completely enthralled with the manipulative brunette and Damon, well, he had fallen head over heels for the brunette vampire. Of course neither brother had admitted back then to knowing that Katherine was a vampire so Ruby had no clue that the brothers had been turned until they both were killed in front of her very eyes. She had been completely heartbroken over the loss of her friends and mourned them until she had received the shock of her life in the form of them waking up so to speak. It was then that she knew for sure that they had been turned into vampires. Ruby had been the one to help the brothers adjust to their new lives as vampires. The feel of an arm sliding around her waist brought Ruby out of her thoughts and she knew it was Damon before he even said a word.

"Damon, how nice of you to join us." Ruby remarked with a playful smirk not taking her eyes off of Stefan.

He smirked and kissed her head softly, "Why thank you, Rubes. Now come on, I never did give you the grand tour of this place."

Stefan watched as Damon whisked Ruby out of the parlor and took that opportunity to run upstairs. He made it to Damon's room in the blink of an eye and looked around only to find Ruby's cell phone on the night stand. Looking down at it, Stefan saw that there was one new text message and flipped the open open as he proceeded to read the text. **Ruby, where the hell are you? **He hesitated before quickly typing in **Mystic Falls, Virginia **and sent the text. Okay granted he didn't know who this Dean guy was that had sent the text to Ruby, but he did know thanks to a drunk Damon once that this guy had been very intimate with Ruby. So naturally the younger Salvatore figured what better way to get Ruby out of town than by bringing her lover to town. Stefan quickly deleted the two texts and set her cell phone back on the night stand before running out of the room undetected. Just in time too since Ruby and Damon fell onto the bed moments later.

Hearing his phone ring, Dean Winchester looked at it only to see that he had finally gotten a text back from Ruby, "Mystic Falls? Yo, Sammy! Where the hell is Mystic Falls, Virginia?"

"Uh, In Virginia?" His younger brother Sam Winchester replied with a smartass smile only to duck the flying pillow headed in the direction of his head.

He rolled his moss green eyes and sighed, "Well look it up, smartass!"

"Alright alright, geez keep your pants on! Okay, it says here that Mystic Falls is a small town in Virginia. Its origins date back to the eighteen hundreds. There was some kind of big vampire massacre type of thing way back then too in Mystic Falls. Although, apparently, there has been attacks every so often since then in and around Mystic Falls." The tall shaggy haired brunette commented as he researched Mystic Falls on his laptop.

That piqued Dean's interests and he sat up fully focused, "What kind of attacks?"

"Well they all seem to be blamed on wild animals, but they could easily be vampire attacks. Sounds just like them at least." Sam remarked with a shrug and looked over at his big brother.

He ran his fingers through his short blonde hair as his mind went over the information he had just acquired, "Why would Ruby be in a town that has had vampire attacks in and around it? SON OF A BITCH! Damon...damn I knew I should of ganked his ass when I had the chance."

Before Sam could even say anything else, Dean was already headed out to the Impala. Sam gathered up his things making sure that nothing was left behind in the small motel room before following his brother out to the car. They had met Damon Salvatore once and it had been quite obvious to Dean that Ruby hadn't wanted them to meet in the first place. Now it was all starting to make sense to him. Luckily for the Winchesters, they weren't far from Mystic Falls and knowing how Dean drives, it wouldn't be surprising if they made it there in less than a couple hours. With Elena busy spending time with her brother today, Stefan was free to hang around the house to keep an eye on things. Of course it wasn't long before he heard the roar of an engine and then a knock at the front door. Ruby and Damon had heard the roar of the engine as well although the slender blonde was convinced that it was simply nothing.

"Oh please, come in. I'm Stefan Salvatore. You must be the Winchester brothers." Stefan greeted the two brother cordially as he held the door open and stepped aside to let them in.

Dean nodded his head looking at Stefan suspiciously as he entered the Salvatore home, "Yeah, I'm Dean and this is my younger brother Sam. Wait, Salvatore? You wouldn't happen to be related to Damon Salvatore would you?"

"As a matter of fact, I am. Damon is my older brother, but I can assure you that I am nothing like my brother." He responded shutting the front door behind them.

He glanced around cautiously at the old fashioned home and then looked over at the younger Salvatore, "Where is she?"

"Upstairs with Damon, I presume. Second door on the right. I wouldn't go up there though if I were you." Stefan remarked fully aware of what his brother and the blonde were probably currently up to at the moment.

Of course his warning seemingly fell upon deaf ears as Dean headed straight up the stairs before either of the other two men could stop him. Unaware of the two new guests in the house, Ruby lay with Damon in his bed basking in the afterglow of their afternoon romp. She always did have a way of wearing him out in bed which was a feat that no other woman had ever really accomplished quite like her. Their bodies intertwined in the crisp white sheets while their clothes lay strewn randomly around the room. Her bright blue eyes fell shut as she finally gave in to her exhaustion. Damon, however, could hear Dean approaching the room and a smirk slowly appeared on his pale handsome face as his eyes opened. In the blink of an eye, Damon was showered and dressed. Ruby still lay intertwined in the crisp white sheets sleeping peacefully and he dared not wake her up because he knew just how vicious she could be if her sleep were interrupted.

Damon opened his bedroom door only to find Dean about to knock, "Well hello Hunter boy. Surprised to see you here."

He narrowed his green eyes at the pale brunette resisting the urge to strangle him, "Where is she?"

His pale soul piercing cerulean eyes stared at Dean for a moment before he shrugged his shoulders gesturing toward the inside of the room, "She's right in there, but I wouldn't bother her if I were you. Ruby hates to be interrupted when she's sleeping."

With that said, Damon walked away with that cocky 'I just got laid' type of grin upon his face as he headed downstairs. Dean rolled his eyes and hesitated before peering into the bedroom. His breath caught in his throat as he caught sight of the beautiful blonde intertwined in the crisp white sheets. She was practically glowing as she slept peacefully unaware of his presence. Shaking his head as he realized what had taken place in that room, Dean headed back downstairs where he found Stefan and Sam speaking peacefully although Damon seemed to be nowhere in sight. Had Dean stayed upstairs a few moments longer, he would of seen the blonde turn in her sleep and heard the name that slipped from her lips in a velvet whisper.

"Dean"


	3. Chapter 3

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Three:

Ruby woke up to find herself alone in Damon's bedroom which didn't really surprise her at all. Her limbs almost felt like Jello, but all it took was one hot shower for the slender blonde to feel like herself again. Of course she also wasn't surprised when she found her bag sitting on the floor at the foot of Damon's bed. After putting her undergarments on, Ruby slid into a pair of denim jeans along with a dark green tank top. She brushed her hair and pulled it back into a ponytail. After adding a little make up to her face, Ruby pulled on her boots and tossed on her black leather jacket before heading downstairs. She could hear the distinctively different male voices as she approached the parlor and her bright blue eyes widened as she saw just who the Salvatore brothers were talking with at the moment.

Damon looked over at her from his seat beside Sam with his ever present smirk upon his face before appearing in front of her in the blink of an eye, "Well well, looks like sleeping beauty finally decided to join us."

"Sam? What are you guys doing here? Are you okay?" Ruby pushed Damon out of the way making a bee line toward Sam.

The older Salvatore brother may of been one of her best friends, but she'd be damned if she'd let him corrupt Sam. To her delight, Sam stood up pulling her into a bear hug and she was relieved to see that he hadn't been compelled by Damon. Her eyes met Dean's and for a moment a wave of guilt washed over her. She pulled away from Sam still confused as to how the Winchesters had found her. Of course that confusion didn't last long as Stefan had chosen that moment to speak up.

"I invited them here, Ruby. I responded to a text on your phone saying you were in Mystic Falls." Stefan admitted looking over at the slender blonde somewhat apologetically.

"You what? Stefan, don't you get it? If I had wanted them to know where I was, I would of told them myself. I swear, Stefan, if anything happens to my boys because they came here, I will stake you so fast even Damon can't stop me." She glared at the younger Salvatore brother allowing her eyes to flicker into their pure black pools of anger.

Before anyone could say anything, Ruby stormed past Stefan shoving him aside and walked out the front door slamming it behind her. Damon and Sam both rolled their eyes before running off after Ruby. Shaking their heads, Stefan and Dean both finished their drinks before following their brothers respectively. Over at the Mystic Grill, Elena was sitting in a booth with Caroline and Bonnie. The young witch was finally back home after being out of town for a while mourning the death of her beloved grandmother. As the three of them chatted together, Ruby entered the place and headed straight for the bar. She downed a few tequila shots before ordering a Jack and Coke. The bartender fixed her drink setting it in front of her as she tossed her money onto the bar. Taking a sip, she spotted Elena out of the corner of her eye and couldn't resist smirking lightly. _Oh Stefan, when will you ever learn to never piss me off? _A smile replaced the smirk as she approached the booth and slid in beside Elena.

"Well hello ladies! Elena, nice to see you again. Oh where are my manners? I'm Ruby." She set her drink down on the table and looked at the two girls across from her.

The young blonde eyed the brash older blonde across from her and then shrugged her shoulders, "Hi. I'm Caroline Forbes. Ruby? Huh, funny, Elena's never mentioned you."

"Nice to meet you, Caroline. She hasn't? Well that's not so surprising. I haven't been in town long and we only just met. I'm a family friend of the Salvatores." Ruby explained taking another sip of her drink.

Bonnie raised her eyebrow at the older blonde curiously, "Really? Oh, I'm Bonnie Bennett."

"The witch, right. Oh don't look so surprised. I can spot a witch a mile away. After all, it takes one to know one." She smiled and took yet another sip of her drink.

Elena's eyes widened as she looked from her friends to Ruby, "You're a witch?"

"Duh! Oh Sam, come on, I was just starting to have fun!" The slender blonde pouted as she saw the tall shaggy haired brunette approaching the booth.

"Yeah, well, no offense Rubes, but your definition of fun is extremely twisted." He remarked watching as she downed the rest of her drink.

Caroline watched this exchanged and smiled batting her eyes softly in Sam's direction, "Well hello there. I'm Caroline Forbes. I don't believe I've seen you around here before."

"Can it, Barbie! He doesn't go for jail bait. I hear Stefan does though. Might want to give him a call." Ruby winked and squealed softly when Sam tossed her over his shoulder.

"Uh, sorry ladies. Enjoy the rest of your, um, night, I guess." Sam stammered before carrying a drunk Ruby out of the building.

It wasn't long before Ruby was back at the boarding house with the Salvatore brothers and the Winchesters. Of course that didn't mean that she was in the same room as all of them. Sam had been kind enough to carry her upstairs and set her down on a bed in one of the guest rooms. He sat beside her in the silence that was soon broken by the sounds of a hiccup followed by a giggle and then the familiar sound of her saying Sammy. It was Dean's nickname for him which he had hated at first, but now it didn't really bother him as much. Dean usually got mad whenever someone other than himself referred to Sam by that name, but he never could quite get mad at Ruby for saying it. Sam gazed down at the drunk blonde sprawled out on the bed and chuckled slightly.

"Sammy, I am serious!" She exclaimed slapping his arm clumsily.

"Okay I'm sorry, Rubes. What's up?" Sam smiled softly and brushed her stray blonde locks away from her face.

"What am I going to do? I love him, but I'm Ruby. I don't do love. I..I'm a bitch." Ruby hiccuped again and frowned softly.

"Maybe you should just tell him and see what happens." He suggested only to hear a knock at the door and laughed slightly as Ruby yelled at Damon to go away.

"Wrong Salvatore." Stefan remarked softly as he poked his head in to look at the pair on the bed.

"Oh. Well then you can come in. I, uh, I'm sorry about earlier. I just didn't want them to hurt you guys and I didn't want Damon to hurt them." She admitted and smiled slightly as Stefan handed her a glass of water.

"Yeah I get that now and I'm sorry too. I never should of invaded your privacy and invited the Winchesters here under false pretenses. I just didn't want you and Damon to burn the town down." He chuckled slightly and watched her take a sip of her water.

"We wouldn't burn the town down. Okay, I wouldn't burn the town down. Now go find your girlfriend. She's probably still freaked after what happened at the grill." Ruby responded with a mischievous smirk.

"Ruby, what did you do?" He groaned slightly as he peered down at the drunk blonde.

"Oh nothing really. Just had a drink with her, Barbie, and the Witch. Oh I may of also let it slip that I'm a witch too and I may of suggested to Barbie that you like jail bait just so she'd stop hitting on Sam." She flashed Stefan an innocent smile and laughed slightly as he disappeared in the blink of an eye.

In the study, Damon poured two glasses of whiskey and handed one to Dean. He looked at the vampire skeptically before taking a sip of his drink. Damon shook his head and chuckled before taking a sip of his own drink. Dean walked around the room glancing around and then looked back at the vampire who had his ever present smirk on his face. His green eyes darkened and he scoffed taking another sip of his drink.

Damon raised his eyebrow and smirked even more as he looked over at the elder Winchester, "You don't know the first think about her, do you?"

A slight smirk graced his handsome face as he took yet another sip of his drink, "I know more than you think."

He nodded his head taking another swig of his drink and gestured toward Dean, "What's her favorite food?"

Dean grinned softly at the thought and shook his head slightly, "French fries that she dips in ketchup. She calls them deep fried crack."

An eerie smile formed on Damon's face as he downed the rest of his drink and slammed the glass down before appearing in front of Dean in the blink of an eye, "Who does Ruby hate more than anyone else in this world?"

His grin faded and he looked straight at Damon fearlessly, "Some skank named Katherine Pierce."

Of course that was all it took for Damon to lose control and an all out brawl broke out right there in the study. The commotion was loud enough for Sam and Ruby to hear which only sobered the slender blonde up before she made a mad dash down the stairs. She and Sam skidded to a stop in the entryway of the study only to see Damon about to sink his fangs into Dean's throat. A gasp escaped from Ruby's lips involuntarily and Damon's head snapped up only to see the horrified look upon the blonde's beautiful face. Tears filled her bright blue eyes which sparkled with a mixture of anger, hurt, worry, and the slightest hint of fear. His vampiric features faded as his eyes stayed focused on Ruby. She stood there for a moment before rushing to Dean's side and she knelt down beside the handsome hunter. Sam followed her blocking Damon from getting near her for the time being. The blue eyed vampire stood there and watched as Ruby cradled Dean's face gently in her hands. She remained like that for a few moments before getting Dean to his feet with help from Sam. They moved him into the parlor and once they got him settled comfortably on the couch, Ruby pulled her phone out and sent a text to Stefan. **Damon n Dean. Big fight in study. **Of course Stefan showed up a few moments later with Elena by his side which resulted in Ruby rolling her eyes.

"What the hell happened?" Stefan asked looking over at Damon who physically looked unharmed.

Damon's soul piercing blue eyes darkened slightly, "I was just testing how well he knew Ruby and I asked him who Ruby hates more than anyone else in the world. He's the one that called Katherine a skank."

"Are you freaking kidding me, Damon? That bitch is a skank and you know it. What? Did that upset your little wittle feelings? Well guess what? Too damn bad! Katherine Pierce is a skank. A blood sucking, centuries living, manipulative, conniving, backstabbing, whorish skank! Stefan knows that, I know that, and we both know full well that you know that. Yeah, that's right, I said it. Katherine Pierce is a skank. Go ahead, Damon, attack me." Ruby snapped getting right up in Damon's face as her bright blue eyes glowed in anger.

His eyes softened as he stared at her and brought his hand up stroking her face softly, "You're beautiful when you're angry."

"Don't touch me." She smacked his hand away from her face and stalked up the stairs.

Stefan was used to seeing them get into fights like this, but he had never seen Ruby quite as passionate with her anger as she was right at this moment. He wasn't surprised though when she returned downstairs with her bag in tow. She followed the Winchesters out to the Impala and tossed her bag into the backseat. Turning around, she wasn't surprised to see Stefan standing nearby. Her anger dissipated a bit and she walked over enveloping the younger vampire in a big hug. She pulled away after a few moments and kissed his cheek softly.

"Keep in touch, okay? You have my number. Oh and princess, take care of my Steffy or I'll come back to kick your ass. That's a promise." Ruby smiled at Stefan and turned her attention to Elena for a moment before hugging Stefan again.

"I will, Ruby, and I'll be fine. So will Damon. You weren't planning on staying angry at him forever were you?" He asked returning her hug and kissing her head softly.

"I don't know, Steffy. I told him not to hurt them and he did. God, I wish he would just get over that skank already. He could do so much better than her." Ruby sighed shaking her head and smiled softly at him before getting into the back seat of the Impala.

"You okay Ruby?" Sam asked as they pulled away from the boarding house.

"Yeah, I will be." She wiped a stray tear away from her face and gazed out the window as the boarding house faded into the distance.

_Dear Diary,_

_So basically all hell broke loose over at the boarding house and now I am headed to who knows where with the Winchesters. I never meant to snap at Damon like that, but he could of killed Dean. I get that he still loves Katherine, but that doesn't mean he has the right to attack anyone who calls her a skank. Okay so granted he didn't attack me, but I always call her a skank. He's used to that by now. I don't know. I'm just confused right now. Oh I'm sure I'll probably end up talking to him sometime soon on the phone, but right now I just need a little space. Okay well we're at the motel and Sammy's going on a food run so I'm going to go take a nap with Dean. _

_Ciao Bitch,_

_Ruby xx_


	4. Chapter 4

**Author's Note: **So I am well aware that I just updated this yesterday, but what can I say? I'm impatient and felt like updating it again lol.

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Four:

"Dean, why did you drive all the way to Mystic Falls? I mean, I get why Sam would, but why you?" Ruby broke the silence in the motel room as she crawled onto the bed after taking her leather jacket off and laid down beside the elder Winchester brother.

He shifted his body a little moving a bit to give her some more room and sighed softly, "Well, you know, Ruby, you're practically like a big sister to that kid and I wasn't about to let him drive to a town that neither of us had ever been to in the Impala."

"Right. So that's why you got into that macho pissing contest with Damon that led to him almost ripping your throat out?" She looked at him skeptically and brushed her blonde locks away from her face.

Dean shrugged his shoulders and looked at her, "Hey, for the record, he started it. I was just defending myself."

"Oh really? Since when is staying still synonoymous with defending yourself?" Ruby asked slightly amused as she moved straddling his hips as her hands rested on his black t shirt clad chest gently.

He rubbed the back of his neck nervously before bringing his hands down to rest on her hips softly, "Well I could of ganked his pasty ass, but I knew you would of been upset if I did that so I tried to fight him off instead. I heard you coming, well, actually I heard Sam. What? You know how clunky his shoes can be. Anyway, I heard him and I stopped trying to fight Damon off because I figured Sam would just knock him away from me. Damon, he tried compelling me, you know."

"Alright well that makes sense I suppose. Wait, how do you know that he didn't compel you?" She inquired staring down at the handsome hunter beneath her touched that he hadn't killed her friend simply because he knew it would upset her.

Dean shrugged his shoulders again and chuckled softly, "When you went upstairs to get your bag, Stefan mentioned that it was a good thing that he had spiked my drinks with vervain. You should of seen the disappointed look on Damon's face."

"Really? Hmm, well remind me to thank Ol' Steffy then." Ruby remarked with a soft smile as she leaned down pressing her lips against his full lips roughly.

His large rough hands slid underneath her dark green tank top brushing against her creamy porcelain skin as he pushed the fabric upward. Ruby broke the the kiss and lifted her arms up allowing him to push the flimsy piece of fabric up over her head. He tossed it aside not caring where it landed and stared up into her bright blue eyes as her fingers played with the hem of his t shirt teasingly. It wasn't the first time that they had found themselves in this position and they knew full well that it wouldn't be the last time either. He had been raised to hunt and kill demons. She was a demon, but somehow they still managed to come together as one in the back of the Impala one night while Sam slept soundly in the motel room. It was only supposed to be that one night of sweet sin and unadulterated passion between them. Of course they never did account for the fact that it was that one night in question that led them to be drawn to each other no matter how hard they tried to fight it.

Somehow Sam always knew when to give them their space for which they were both grateful for since neither of them wanted to scar the poor guy for life. Their skin glistened with sweat and their chests heaved as they tried to catch their breaths. As she lay contently in his arms, Ruby couldn't help comparing Dean and Damon in her mind which made her feel guilty considering what she had just done with Dean. Granted, both men were amazing lovers, but somehow she always ended up being held by Dean as they basked in the afterglow of their lovemaking. She surprisingly loved to cuddle after getting laid although she'd never admit that out loud. Damon never cuddled with her though, but Dean always did.

Clearing those thoughts from her mind, Ruby snuggled into Dean's side and drifted off to sleep. Back in Mystic Falls, however, Stefan watched as Damon sat in the study broodingly staring at the fire that was crackling in the fireplace. He had been broody since Ruby had left and Stefan was worried as he knew how bad Damon could get when he was upset. The younger Salvatore sat down in the chair opposite of Damon and sighed softly.

"Just give her some time to cool off, Damon. I'm sure she'll talk to you soon." Stefan assured his older brother who sat stoically with a glass of scotch in his hand.

Damon took a swig of his scotch and scoffed, "I hate witches."

"Come on, Damon, you don't mean that. You and I both know that you don't hate Ruby." He remarked and shook his head.

The blue eyed older vampire shrugged his shoulders and downed the rest of his scotch, "Alright, maybe I don't hate her, but come on! She just doesn't get it when it comes to Katherine. Yeah, I know how bad Katherine is, but I still loved her. Ruby has never been in love. What does she know about it?"

"More than you'd think, brother. I, uh, overheard her telling Sam that she loved someone. She didn't say who exactly. Just that it was a him." He remarked and smiled slightly as Damon appeared to perk up a bit.

His pale cerulean eyes sparkled as the reflection of the flames danced within them, "Interesting. Well we all know she meant me, Stefan."

"Right. Believe what you want to believe, Damon. What the.." Stefan rolled his eyes as the ever present smirk returned to Damon's face and then glanced around cautiously as the lights began to flicker.

The smirk faded as his eyes widened making him look as if he were processing his thoughts, "Katherine?"

Standing in the entryway behind them, an exact replica of Elena stood with an eerie smirk upon her face, "Well hello boys. Did you miss me?"

As he shut the motel room door behind him, Sam cracked a smile and shook his head as he spotted his brother asleep with a sleeping Ruby beside him. The tall shaggy haired brunette locked the door grateful that they were at least mostly covered up and made his way into the bathroom. He walked back out a few minutes later in a grey muscle tank top and plaid pajama pants. Sliding into his bed, He got comfortable and yawned softly as he nestled his head into his pillow after attaching his cell phone to its charger. Sam glanced across from him and noticed the expression on Ruby's face. Grabbing his phone, He snapped a picture of Ruby and smiled to himself as he set his phone back down. Hey, it wasn't every day that he saw her looking so peaceful with a content smile upon her face. He sighed slightly and shut his eyes falling asleep moments later. Back at the boarding house, things were rather silent aside from the sound of the fire crackling as the brunette stood by herself in the study.

Her chocolate brown eyes glowed eerily as the reflection of the flames danced within them as she tossed a photograph into the fire, "Poor pathetic little Ruby. When will you learn that you are just no match for Katherine Pierce? You are such a weakling that it is pathetic to even consider you as being a witch. Oh, that's right, they call you a demon now. Kind of fitting, is it not? Those boys are mine and there is nothing you can do to change that. Time is running out for you and you don't even know it yet. How fun! See you soon, Ruby. Tick Tock, Tick Tock, Tick Tock."

As she cackled evilly, the brunette stared down into the flames as the fire took its toll on the photograph. It was of Stefan, Ruby, and Damon in that order. She smirked happily as the images of the Salvatore brothers were burnt to a crisp and her eyes widened in delight as the flames encircled the image of Ruby. She cackled even more as the image of Ruby was burnt beyond recognition. All that was left of the photograph by then was a pile of black ash. An eerie smirk appeared on her face just then as she doused the flames putting the fire out completely. Turning on her heel, She walked upstairs to Stefan's room and smiled at the sight of the boys all tied up.

"Untie us, Katherine." Stefan growled knowing just how dangerous the brunette could be.

She laughed slightly and shook her head, "I'm afraid I can't do that just yet, Stefan. What's the matter? Don't like the vervain infused rope? If you think that's bad, wait until you see what I do to Ruby. She'll never know what hit her. I'm going to do to her what no other person has ever done before."

"Oh really? And what might that be?" He questioned fully aware of how Damon was silently glaring at Katherine.

The brunette smirked confidently at the vampire brothers and spoke up in an eerily lethal tone, "I am going to break her. Just you wait and see."


	5. Chapter 5

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Five:

Having not seen Stefan for most of the day or Damon for that matter, Elena Gilbert parked her car outside of the Salvatore boarding house and walked up to the front door. She began to knock on the door only to watch as it opened slightly on its own. The brunette pushed the door open and peered inside before taking a step into the house. It was rather quiet and no one seemed to be around. She headed up the stairs to Stefan's bedroom and gasped at what she found when she got to the open doorway of the bedroom. There were two broken wooden chairs and a large bloodstain on the carpet near one of the chairs. Resting near the edge of the bloodstain was a sprig of what Elena instantly recognized as being vervain. The sound of a cell phone ringing startled her and she glanced around only to see Stefan's cell phone on the ground. She knelt down picking it up only to see Ruby's name on the display and pressed the answer call button.

Her hand shook slightly as she raised the cell phone to her ear, "Ruby? It's Elena."

"Elena? Wait, what's wrong? Where's Stefan?" She spoke rather nicely to the brunette for once as she grew concerned by the panic that was obvious in the young girl's voice.

Elena ran her fingers through her long brown hair and sighed, "I..I don't know, Ruby. I haven't seen him or Damon all day so I came here to the boarding house. The front door wasn't even closed all the way when I knocked on it. The place is real quiet and everything seems okay except for Stefan's room."

"What's wrong with Stefan's room, Elena?" Ruby sat up straighter as Sam looked over at her with a concerned look upon his face.

She walked out of the room and headed back down the stairs, "It's a mess. There are two broken wooden chairs in there. There's a bloodstain and there was a sprig of vervain near that bloodstain."

"Listen to me, Elena. You need to get out of that house right now, get in your car and drive to somewhere safe alright?" She instructed the young girl as she stood up and began to pace not even noticing that Castiel had just vanished from the room.

Elena nodded even though she knew that the blonde couldn't see her and walked toward the front door, "Okay, but what about.."

"About what? Elena? Hello? Are you there?" Ruby called out into the phone only to hear a scream, some muffling, and the sound of heels.

A smirk formed on the brunette's face as she knelt down to pick up the phone and then placed it to her ear, "Well hello Ruby. Long time no talk. I'll tell the boys that you said hello. By the way, how are Sam and Dean?"

"YOU BITCH! I swear I'll..Dammit!" Her face paled noticeably as she yelled into the phone only to hear the dial tone.

Ruby hung up the phone and glanced up just in time to see Castiel appear with a frightened Elena in tow. The brunette practically ran from the angel and hugged Ruby who was too stunned to react in any way other than to return the hug. Katherine had already gotten to Stefan and Damon. She knew now that the brunette bitch was well aware of the Winchesters and Ruby would be damned if she was going to let Katherine get anywhere near the handsome hunters. She pushed Elena away slightly and sighed.

"Relax Elena, that's Castiel. He really is an angel. We'll get you back to Mystic Falls and find the boys, don't worry." The blonde assured the young girl and sighed as she tossed on her black leather jacket.

"Ruby, what's going on? Where are you going?" Sam questioned the blonde as he watched her walk toward the door of their motel room.

"I need a map. Look, Stefan and Damon were turned by this bitch named Katherine. She looks practically identical to Elena and she has those boys somewhere. She knows about you two so please just stay here and whatever you do please do not open that door for anyone other than me." Ruby gave the Winchesters a serious look before flashing Castiel a thankful look.

She grabbed Elena's hand and walked out of the motel room slamming the door behind her. Sure, Ruby didn't really care much for Elena, but she knew that the girl obviously cared a lot about Stefan as did he about her so for now Ruby was going to protect her. Elena let Ruby pull her into a store and watched as Ruby looked through maps obviously trying to find a certain one. The brunette was confused as to how a map could possibly help find Stefan and Damon. Ruby picked up on that confusion though and scoffed slightly.

The brunette continued to watch her and finally decided to ask the question that was bugging her, "How the hell is a map supposed to help us find Stefan and Damon?"

"Remember when I told you and your little friends that I was a witch? Yeah well I know how to use a map to determine the exact location of someone. It doesn't take long, trust me." She responded in a hushed tone although she purposely left out the part about how she had never tried using this method before to find vampires.

Ruby found the maps of Virginia that she had been looking for and paid for it. She practically dragged Elena back out of the store and they headed back to the motel. Naturally, they ran into Dean as they got to the door and Ruby rolled her eyes when she saw that he had made a food run. Of course he'd be the one not to listen when she said to stay put. Her annoyance with him, however, seemingly melted away when he handed her a bag full of fries. She smiled and ate as she set the current map of Virginia up for what she had to do. Once she was ready, she began to chant as she held Dean's lighter to one corner of the map. The edges began to burn and she flicked the lighter closed as she continued to chant. After a few moments, she said the word 'out' and the flames vanished leaving behind a map that was virtually unreadable with the exception of one clear spot on the map. Ruby repeated this process with the antique map and the same thing happened. She compared the two and her face grew even paler when she realized what she was seeing.

Elena finished her burger and took a sip of her soda as she looked over at Ruby, "Well what does it say? Do you know where they are?"

"Yeah, I do. She has them over at the Covington Home for Orphaned Children or at least what's left of it anyway. It's actually not that far from the boarding house." The slender blonde responded as Dean glanced over her shoulder at the maps.

He rested his chin on her leather clad shoulder for a moment and then kissed her cheek softly, "How can you tell? Neither map says what exactly is in that spot."

"I know because that's where I was raised. My mother was young when she gave birth to me. Barely sixteen at the time and in those days a child out of wedlock automatically gave you the label of whore. My grandparents didn't really approve of my father. Different social classes, you know, and he got enlisted into the war. Mom's last gift to him before he left for the war was her virginity. She found out she was pregnant the same day she found out that he had been killed in battle. My rich grandparents kept my mother's pregnancy a secret and I was in the orphanage soon after I was born. People tried to adopt me over the years, but the Covington family, the rich folk that ran the orphanage, always claimed that I was in the process of being adopted." Ruby explained pausing to take a sip of her soda.

Dean sighed inwardly and wrapped his arms around her thin waist from behind, "Go on, Rubes."

"Alright, well, their daughter always paid special attention to me and I had always hoped that maybe if I was lucky enough that she'd adopt me. When I was seven years old, she finally found out about the harsh conditions that us orphans were really living under. By then her parents had passed on and she along with her siblings inherited the orphanage amongst other things. Well, that day that she saw that orphanage for the horror that it really was, she picked me up in her arms and sobbed begging for forgiveness. Turns out that Sarah Covington, the youngest Covington, was my birth mother." She leaned back against Dean's chest and sighed wiping away a few stray tears that had begun to fall.

"Wow. Ruby, we didn't know. Why would Katherine take the Salvatore brothers there though?" Sam asked looking over at the blonde sympathetically.

"Because that's where she killed my mother, Sam. Katherine hated the fact that I was closer to Stefan and Damon than she was at the time. My mother was overseeing renovations to that damned orphanage. The boys had been helping out and that bitch showed up. I was outside pouring some lemonade for the boys. I heard my mother scream and I dropped the pitcher of lemonade as I ran inside. I found her on the floor with most of her blood drained out. She was bitten and Katherine was nowhere to be found. I refused to leave my mother's side and a fire broke out. The Salvatore brothers noticed it before I did. I still refused to leave her side though. They grabbed me though and had to drag me out. I was practically kicking and screaming. I saw my mother burn and I swear I saw her. I saw Katherine smirk at me with her blood stained lips before she disappeared. Her turning Stefan and Damon into vampires later on just made me hate her even more." Ruby finished explaining only to end up on the receiving end of a Winchester group hug.

Elena stayed quiet as her mind processed the information she had just learned and then spoke up as Sam pulled away from Ruby, "So what's the plan? How are we going to save Stefan and Damon?"

"We aren't going to do anything, Elena. I am returning you to Mystic Falls and then I'm going after Katherine myself. I'm not letting her get to Sam and Dean too." Ruby remarked in an eerily lethal tone as she glanced over at Elena.

Dean's eyes widened upon hearing that and he shook his head, "No Ruby, you are not going after her alone. We've ganked vampires before and we'll do it again if we have to. I'm..We're not letting you go alone."

"She knows about you and Sam. I'm sure she's counting on you two tagging along with me. I'm not letting you two get hurt because of me. Just get as far away from Virginia as you can and be careful." She hugged Sam and then stood in front of Dean.

He rested his forehead against hers as his eyes pleaded with her not to go alone. She flashed him an apologetic look before leaning up and pressing her lips to his lips in a searing kiss. Ruby knew that there was a chance that she may not make it back to them alive and she wasn't about to leave without kissing him goodbye. She pulled away and walked over to Elena taking a hold of her hand. Ruby looked over at Castiel and he nodded his head at her. The blue eyed angel pressed his fingers to their foreheads and just like that all three of them vanished from the hotel room leaving the Winchester brothers behind.

"Dean, what the hell are you doing?" Sam questioned his older brother as he watched him gather their things.

The elder Winchester threw their stuff into the Impala and started the car, "What does it look like I'm doing, Sammy? There's no way in hell that I am letting her go there on her own. Now get your ass in the car or you're hitchhiking."

"Look, I know you don't want to hear it, but maybe she's right, Dean. I mean, Ruby knows this chick better than either of us do. Maybe we should actually listen to Ruby for once." He tried to reason with his brother as he got into the car.

He paused and turned to look at Sam with an incredulous look upon his face, "Seriously, Sam?"

"No, you're right. Step on it." He conceded as he buckled his seatbelt.

The Winchesters arrived in Mystic Falls in under two hours courtesy of Dean's fast driving. They were driving down a main road that was lined by trees on either side of it for as far as the eye could see. Something suddenly darted out in front of the Impala and Dean slammed on the brakes only to see that their was a frightened Elena a mere few inches from the car. She was wearing the same thing that she had worn when they had last saw her, but now she was covered in blood. There were no other cars for miles so he opened the door and glanced around wondering where the hell Ruby was at the moment.

The frightened brunette rushed up to him with tears sparkling in her eyes, "It was so horrible! It was Katherine. She was waiting for us and she attacked. She has Stefan and Damon tied up. I..I'm covered in Ruby's blood. She's so pale. Katherine's forcing them to watch her get tortured to death. They are in that direction. You can't miss it."

Not hesitating for a moment, Dean took off in the direction that Elena had pointed out intent on getting to Ruby in time. Sam got out of the car as well and looked around. Elena seemed to be trying to get him to go in the same direction that Dean had just went in. He started to walk that way when it suddenly hit him. She had mentioned that they were attacked, but only mentioned herself along with Ruby. The brunette had never mentioned Castiel and Sam knew that Cas would of tried to protect the girls at least. He turned around to face the brunette only to find her staring into his eyes.

Her eyes widened a bit as she spoke softly, "You will not remember this. You will follow your brother and do as I say."

"Uh, no, I won't. What the hell are you trying to do, Elena or should I say Katherine?" He asked before trying to attack her.

Katherine smirked and managed to fight him off before knocking him out. She reached into the car turning it off and then dragged Sam into the woods. After ensuring that the real Elena was safe and sound for the night, Ruby disappeared with Castiel. The sun was just starting to rise when they finally reached the point of the road where the Impala was sitting by itself and Ruby's face paled when she realized that there was no one in the car. She glanced around not seeing any sign of them and tried not to panic.

Castiel noticed the pavement particularly around the Impala and frowned, "There's blood. Here on the pavement in front of the car and right there on the pavement next to the driver's side door. It's not theirs."

"Cas, I need you to take me to that orphanage, please. It's the only way to save them."


	6. Chapter 6

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Six:

As much as he wanted to save the Winchesters, Castiel knew that he couldn't just bring Ruby there by herself especially after Katherine had just proved to be strong enough to kidnap two hunters and two vampires by herself. Instead, Cas transported them to Elena's house where the young brunette was in the kitchen with her two friends Caroline and Bonnie. The blonde demon was about to flip out on the trench coat clad angel only to fixate on Bonnie instead as a plan began to formulate in her mind.

"Bonnie, I need your help. I need your magical help." Ruby admitted as she stood across from where the young brunette was sitting.

The young witch eyed the blonde demon skeptically before biting her lip, "If it's to help Damon, I won't do it. Last time I did that, my grandmother died because she helped me help him."

"Look, It's not just Damon okay? It's Stefan too. This evil vamp bitch from their past kidnapped them along with my friends Sam and Dean who aren't vampires by the way. Those four guys are all the family that I got so I am begging you please to help me save them." Ruby really truly hated to beg, but this time she was really desperate.

Bonnie considered her words and then nodded her head slowly, "Alright, I'm in. How can I help?"

As Ruby went over her plan with the group, Damon was watching as Katherine paced back and forth in front of him. He knew that she was expecting Ruby to burst in there ready to kick some ass and yet he was surprised that the blonde demon hadn't shown up yet. He briefly considered the notion that maybe Ruby was still mad at him for the fight with Dean, but spotting the elder Winchester brother across from him quickly cleared that notion right from his mind. Damon realized that if Katherine had gotten to Dean then that meant she had also more than likely gotten to Sam and he knew that if Ruby wasn't pissed before, she was going to be borderline lethal when she found out that Katherine had gotten all four men.

He stared over at the sadistic beauty and narrowed his pale blue eyes slightly, "Let them go, Katherine. They didn't ask for this and they don't even know you."

Katherine finally stopped pacing and walked over to Damon grabbing his face with her hand forcing him to look at her, "They know Ruby. Don't you get it? This isn't about me. This is about Ruby. That blonde demonic whore is finally going to get what's coming to her. Oh I just wish you could see the look on her face when she finds Sam."

His moss green eyes snapped open and darkened with anger, "You bitch! What did you do to my brother?"

A sinister smile grew upon her face and she cackled softly, "Oh quit your whining, Winchester. Your brother is fine. He's just taking a little nap. Don't you worry, Ruby will find him. She knows that spot all too well."

Realization sank in for Damon and he struggled against the ropes that binded him, "Katherine, stop this now. Look, you can have me. Just let them go."

Katherine shook her head and let go of Damon's face, "Oh no, now what fun would that be? You're already mine, Damon, and once I destroy that witch we'll both be happy."

Damon glared at Katherine in anger only for some of that anger to melt away as her lips met his in a soft kiss. Ruby, meanwhile, arrived with Bonnie outside the old orphanage courtesy of Castiel. As per the plan, He was to stay outside with Bonnie while Ruby headed inside by herself. The blonde demon was decked out in all black: black leather jacket, black shirt, black pants, and black boots. The clouds overhead darkened the area which at least gave the three of them some kind of camouflage. The angel and the young witch stayed out of sight as Ruby approached the front door slowly. Taking a deep breath, she steeled her nerves and kicked the door open. It landed on the floor with a thud and after the cloud of dust dissipated, Ruby walked in over the door and glanced around. It was mostly dark with the exception of a few strategically placed torches and candles. As she walked further inside, the blonde came face to face with Stefan Salvatore who was hanging from the ceiling by a vervain laced rope.

"Oh god, Stefan! Hey, hey, can you hear me? It's Ruby." She tilted his face up trying to get his attention as she whipped her demon killing knife out and cut the rope in one swipe.

"Ruby? No, no, It's a trap. She..She's trying to..break..you." Stefan barely got out as he practically collapsed onto her.

"I know Steffy, but I'm a lot tougher than she thinks." Ruby remarked confidently as she shoved the younger vampire off of her and pulled out a plastic bottle filled with animal blood.

The blonde knew full well that the blood would help him get his strength back up and it hadn't been easy acquiring this blood either. She unscrewed the cap and waved it under his nose before bringing it down to his lips. Ruby tilted the bottle slowly letting Stefan get a taste of the blood and soon enough he was holding the bottle himself. A sigh of relief escaped from her own lips as he stood up on his own before helping her to her feet. They hugged and then Ruby walked further into the mostly destroyed building. Stefan followed her though he wasn't back at full strength which didn't seem to bother him as he was intent on not letting Ruby go through this alone as he knew of Katherine's plan. A horrified gasp abruptly pulled Stefan from his thoughts and he looked ahead of him only to see the body of a tall shaggy haired man laying limply in the center of the room that they were currently walking through. It then hit him as he realized why Sam Winchester was laying in that position in that exact spot. Stefan could remember as if it were yesterday the image of the pale beautiful blue eyed blonde laying in that spot in the same exact position with two bloody puncture wounds in her neck. Her lifeless eyes just staring at him as her daughter broke down in sobs beside her body.

"No, no, Sam, this can not be happening again! No, no, not Sammy! I..I can't lose you too, Sam." Ruby dropped to her knees beside Sam's body fighting back sobs as her trembling hand reached out to feel his neck.

"Ruby.." Stefan trailed off not knowing what to say to comfort the blonde.

"There's no blood. Stefan, there's no blood! She didn't bite him. Oh god, he's alive! Come on, Sammy, wake up." She moved his head onto her lap gently and brushed his brown locks away from his handsome face relieved that he hadn't suffered the same fate that her mother had.

Stefan kept an eye out for Katherine while simultaneously keeping an eye on Ruby and Sam. It wasn't long before the young hunter's eyes slowly began to open. He blinked a few times and rubbed his eyes before realizing that Ruby was staring down at him. Her face was much paler than usual which concerned him as he sat up slowly and turned to look at her.

"Hey kiddo. You alright? You scared me there for a second." She smiled slightly as she fought back the tears that threatened to fall from her darkened blue eyes.

"Yeah, I think. Where's Dean? We thought she was Elena and he took off into the woods after you because she said that you two had gotten attacked. I realized she wasn't Elena because she only mentioned the two of you and didn't mention..so we fought and I got knocked out." Sam explained as Ruby pulled him into a nearly bone crushing hug which he of course returned.

"We're fine, Sam. Elena is somewhere safe and Dean, well, I don't know. I can only assume he's here somewhere with Damon. Can you stand?" She asked as she pulled away and stood up glancing down at Sam.

"Yeah, I'm fine Rubes. Let's just go find them before one of them does something stupid." He remarked as he stood up with a little help from Stefan.

Ruby was relieved that Sam was okay, but as she glanced around she could feel her anger rushing back through her veins. With help from Sam and Stefan, Ruby searched the rest of the orphanage only to come up empty. The brunette watched them from afar annoyed that Ruby wasn't a sobbing mess by now. It was alright though because as far as Katherine was concerned, she was positive she had the ace up her sleeve so to speak.

The brunette smirked softly as she placed her hands on her hips, "Looking for something?"

"Where are they, Katherine?" Ruby glared over at Katherine as she began to storm toward the wicked brunette.

She threw her hands in the air and shrugged her shoulders, "As if I would actually tell you. No, I won't. First, we're going to play a little game and then maybe if I'm feeling nice, I'll let one of them go."

"No games, you conniving bitch!" She snapped only to growl when Katherine disappeared in the blink of an eye.

The brunette vampire appeared even farther away from Ruby and smiled tauntingly at the blonde, "It's very simple Ruby. All you have to do is make a choice. Dean Winchester or Damon Salvatore? The Hunter of The Vampire? What will it be? Oh of course you should probably know the stipulations."

"Screw your stipulations!" Ruby snapped again and threw her knife at Katherine only to stab the vampire in her shoulder.

Katherine pulled the knife out of her shoulder slowly and licked the blood off of the blade before throwing it back at Ruby, "Well ow. Anyway as I was saying, there are stipulations for you to consider. If you choose the hunter, both Salvatore brothers will be condemned to spend an eternity with yours truly. However, if you choose the vampire, well, that hunky hunter will be condemned to spending an eternity as a vampire."

"What? No, you can't do that, Katherine!" Her eyes turned into pure black pools full of anger and hatred which was directed at Katherine as Stefan caught the knife that nearly stabbed Ruby.

The brunette vampire rolled her eyes and scoffed, "You try my patience, demon. Make your choice. Who will it be? Dean or Damon?"


	7. Chapter 7

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Seven:

"Where are they?" Ruby demanded glaring at the brunette vampire in such a way that if glares could kill, the vampire would be dead on the spot.

Katherine merely scoffed and gestured to either side of the room, "Damon's right there and Dean is directly across from him."

Sure enough, as more candles became lit around the orphanage courtesy of Bonnie's magical assistance, Ruby's bright blue eyes widened in horror at the sight of both Damon and Dean tied up. Of course there was no way that Stefan could use his vampiric speed to get over to Damon and untie him due to the fact that the rope used to tie Damon up was laced in vervain. Another plan formed in the blonde demon's mind and she slipped the bottle of human blood to Sam. She glanced at Stefan gesturing to Sam before gesturing to Damon. The younger Salvatore stared at her blankly for a moment before his mind registered what she was trying to tell him and then he nodded his head in understanding. Stefan may not of been able to touch the vervain laced rope without being weakened, but Sam could. Ruby knew that Sam could easily go untie Dean once he was done untying Damon so she focused her attention on Katherine. Unfortunately the brunette vampire was two steps ahead of her and used her vampiric speed to appear right beside Dean.

She tilted the elder Winchester's head away from her and brushed her fingertips against his neck as her fangs appeared, "Go ahead and untie Damon. I'll just enjoy a little snack over here."

"Don't you dare. Stay away from him, Katherine." Ruby warned the brunette vampire in a calm yet lethal tone.

Katherine's lips twisted into a smirk as she tauntingly hovered her fangs over his neck, "Ah ah, you didn't make your choice, demon."

"Fine. I choose him. I choose Dean. Now stay the hell away from him." She snapped surprising everyone in the room as no one had actually expected her to choose.

A sinister grin replaced the smirk upon Katherine's face as she retracted her fangs and took a step back from Dean, "Excellent choice, Ruby, but I'm afraid you took too long in choosing so therefore I've decided to keep both of them along with Stefan."

Of course with her attention on Ruby and Dean, Katherine had failed to notice that Sam had successfully untied Damon. He unscrewed the top off of the plastic bottle that Ruby had given him and brought it to the older Salvatore brother's lips. The scent of the blood alone caught Damon's attention instantly. It was spicy yet sinfully sweet at the same time. As he drank from the bottle, he savored the taste of what he knew to be demon blood, It was spicy like chili yet rich like chocolate. Best of both worlds in his opinion. He knew it had to be Ruby's because she was the only one in the vicinity with demon blood within her aside from Sam and he knew full well that she would never let him drink Sam's blood. Of course it hurt to hear Ruby say she chose Dean, but he also saw with his own eyes that Katherine had manipulated her into choosing Dean over him.

"Oh yeah? Well I'm afraid that the only way you are getting all three of them is over my dead body, you scum sucking skank!" Her lips twisted into a smirk as she glared at the brunette vampire.

A delighted smile appeared on her face creepily as she looked over at Ruby, "Over your dead body? It'll be my pleasure."

With that, the vampire ran toward Ruby knocking the blonde demon to the ground and let her fangs show as she was prepared to rip out the blonde's throat. Ruby struggled with the female vampire and knocked her away only to pull out a third bottle filled with blood as she stood up. Of course Katherine charged at her again knocking her down causing the bottle to fall out of her hand. As she struggled with the female vampire, Ruby clawed at the ground with one hand trying to find the bottle. When she finally grasped it, Ruby unscrewed the top and shoved the open end of the bottle into Katherine's mouth.

"Bottom's up, Bitch!" Ruby smirked as the vervain laced blood flowed into Katherine's mouth and down her throat.

The brunette vampire shoved the blonde demon away and collapsed to her knees gagging violently. Seeing Sam untie Dean, Ruby grinned and delivered a nice swift kick to Katherine's ribs. She delivered a second one much to the displeasure of the female vampire and went to kick her a third time only for Katherine to catch her foot mid kick. Ruby landed on the floor on her back and it turned into an all out vicious cat fight so to speak. Damon reached them before anyone else could and froze as he tried to decide who to grab. He caught Ruby's eye and took a deep breath before wrapping his arms around Katherine's waist disentangling her from the demonic blonde. He took a few steps back with a struggling Katherine still in his arms and watched as Ruby got to her feet. Reaching out, Ruby ripped the necklace off of the female vampire's neck and tossed it into a nearby flame watching it begin to melt before turning her attention back to Katherine. She pulled out a wooden stake and twirled it with her hand.

Damon stared at her pleadingly over the brunette vampire's shoulder, "Ruby, please, don't."

"That was for Sam. That was for Dean. That was for Stefan. That was for Damon. That was for me." She spoke in a rather lethal tone as she punched Katherine repeatedly in the face.

His pale cerulean eyes became glassy as he continued to stare pleadingly at Ruby, "Don't."

"And this is for my mother!" Ruby declared as she drove the wooden stake straight into Katherine's cold black undead heart.

A gasp slipped past her blood stained lips as her chocolate brown eyes widened in shock. Damon looked at Ruby horrified at what she had just done and held the brunette female vampire as her body slumped in his arms. Deep down he knew what Ruby had done was the right thing, but he never truly did get over Katherine so the thought of her being gone for real hurt him immensely. Ruby watched helplessly as Damon laid Katherine's limp body flat on the ground and she bit her lip watching the blue eyed vampire as he wept for his former love. She knew they couldn't just leave the body laying there though so when Stefan pulled Damon aside, Ruby squirted a little lighter fluid over Katherine. She was about to light the corpse on fire when out of nowhere a fist full of salt covered the body. The blonde demon glanced up only to meet Dean's eyes. He simply shrugged his shoulders flashing her a sheepish smile and she shook her head in response. Lighting the match, she eyed the flame for a moment before tossing it down onto Katherine. The corpse burst into flames which garnered a scream of horror from Damon.

He pushed past Stefan walking around the burning corpse and approached Ruby grabbing her by her upper arms, "How could you? What? Killing her wasn't enough so you had to go burn her too?"

"I..Damon, stop it! You're hurting me!" Ruby, as tough as she was, gazed up at Damon for the first time with genuine fear shining brightly in her eyes.

Growling, he tossed her aside like a rag doll causing her to collide with a wall. At that moment, Castiel barged into the room with his trench coat billowing behind him. It took all the strength within him to prevent Dean from ripping Damon's head off. Sam, however, knelt down beside a half conscious Ruby unable to see any outward signs of injury although he was pretty sure that her ribs were at least bruised if not broken. He gently wrapped one of his long arms around her back and his other arm under her legs lifting her as he stood back up. She snuggled into him wincing as she did so and rested her head against his shoulder.

Castiel finally got Dean calmed down some and glanced around at everyone, "We need to go now. Bonnie's powers are unstable and she can't hold it off much longer."

Seeing that Ruby was safe in Sam's arms, Dean nodded his head at the angel and headed out of the orphanage. Bonnie sighed inwardly of relief as she watched the Winchesters walk out of the building along with Ruby and Castiel. She continued chanting as they reached the safe distance that she was standing in only to watch in horror as the building exploded right before their eyes. All the young witch could think of was how heartbroken her best friend was going to be when she learned of Stefan's tragic fate. Ruby, however, was wincing majorly as she tried to fight her way out of Sam's arms. Seeing this, Castiel walked over and pressed his fingertips to her shoulder causing the blonde to slump over in Sam's arms completely passed out.

"So what are we all watching?"

Hearing his voice, Bonnie looked over at Damon only to see him standing beside her with Stefan and she rolled her eyes at the older Salvatore, "Damon, you are such an ass!"


	8. Chapter 8

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Eight:

When Ruby finally awoke, she glanced around at her surroundings only to be surprised when she found herself in a bedroom that she didn't recognize. She wasn't sure how she got to wherever she was considering the last thing she remembered was watching the orphanage explode. The blonde demon sat up abruptly as her bright blue eyes widened in panic as it all came rushing back to her. The slender brunette who looked identical to Katherine yet nowhere near as evil sat down on the edge of her bed and smiled softly at Ruby. The blonde winced slightly and rested her hand against her midsection lightly.

Elena handed her the ice pack wrapped in a cloth and eyed her with concern, "It's alright, Ruby. The guys are fine. Sam and Dean are downstairs. Stefan is over at the boarding house with Damon."

"Elena? Where am I? How did I get here?" She asked looking at the brunette confused yet relieved to hear that the guys were okay.

The young brunette smiled softly and gestured around the room, "This is my bedroom. Stefan led the Winchesters over here with you. I mean, you were in bad shape, Ruby, and you did save my boyfriend so how could I not let you rest in here?"

"Uh thanks, Elena. I guess you're not as bad as I thought you were." Ruby smirked slightly and then winced again.

Castiel knocked on the open door just then and stayed in the doorway as both women looked over at him, "Ruby, how are you feeling?"

"How do you think I'm feeling, Cas? Like a truck ran over me. Can't you please do something about this?" She glanced over at him with pleading eyes as she gestured to her injured midsection.

He looked to Elena knowing that it was her room and she simply nodded her head gesturing for him to come in. She moved letting him have some room to take care of Ruby and watched in amazement as he hovered his hand over her midsection healing the blonde without even touching her. Ruby let out a sigh of relief and smiled gratefully at Cas. She was still sore, but it was nowhere near as painful as before.

The blue eyed angel stepped back and steadied Ruby as she stood up, "Take it easy. Because you're a demon, I can't heal you fully, but I was able to make it so that your ribs weren't broken just bruised."

"Thank you. I appreciate that, Castiel." She smiled at him and was then surprised when she found herself downstairs in the blink of an eye along with Elena.

Ruby glanced around and somehow wasn't surprised to find Dean sitting at the kitchen table flirting with Elena's Aunt Jenna. She narrowed her eyes at the sight only for it to be blocked a moment later as she was enveloped in a big hug by a rather tall Winchester. Ruby grimaced as she felt the pressure against her sore ribs and sighed softly as he pulled away from her. It was then that she noticed that Castiel was sitting at the table with Jenna and Dean.

"Hey Sammy. Relax, I'm fine. Cas was able to downgrade me from broken ribs to bruised ribs. I'll be fine once they heal completely." The demonic blonde assured him and smiled softly.

"Well thank god. You hungry? Thirsty? Anything?" Sam asked as he tried to get her to sit down and relax.

"No, I mean it, I'm fine. Actually, I want to go over to the boarding house. I have to see Stefan and Damon." She remarked refusing to sit down even though she appreciated Sam's concern.

Dean, however, heard Ruby's voice and his head snapped up at the mention of the Salvatore brothers, "No, absolutely not, Ruby. Not after what that monster did to you."

"I am not arguing with you, Dean. It hurts a bit to even breath let alone talk and don't call him that. You don't know him like I do." Her voice was calm yet lethal as she leaned against the couch slightly.

He stood up walking over to her and sighed, "I don't want you to get hurt."

"Yeah I know and I appreciate that. It's not like I'm going to be alone with Damon though. After what happened, Stefan would never allow it unless he was certain that Damon wouldn't hurt me." She assured the elder Winchester brother and smiled softly.

Dean nodded his head and sighed reluctantly, "Fine, but I'm going with you."

"Ugh, fine. Let me just go call Stefan first to let him know we're coming over." Ruby scoffed slightly as she headed to the bathroom to freshen up and then smiled as she headed out the front door.

He shook his head chuckling slightly and informed everyone that he was going to the boarding house with Ruby. The all too familiar roar of a certain engine caught his attention and everyone ran after Dean as he ran outside of the house. He got out the front door just in time to see Ruby drive away in the Impala. Patting his pockets, His eyes widened as his face paled. She snaked his keys and drove off in his baby.

Dean glared slightly at Sam who was fighting back a laugh and looked back at the road, "Son of a bitch! If there is one scratch on that car, I am so going to kill her!"

"Sure you will." Sam spoke up before laughing out loud not too worried about Ruby going off alone since he knew Stefan wouldn't let anything happen to her.

The somewhat familiar roar of a car engine caught Stefan's attention and he cursed his luck as he noticed the sinister smirk form on Damon's face. He really didn't feel like breaking up a fight between his brother and Dean Winchester today. Damon walked over to the front door swinging it open and stepped out into the bright sunlight watching the driver's side door of the Impala open. His smirk faded however as the blonde demon stepped out of the car wincing slightly. The vampire instinctively ran to her using his vampiric speed and helped steady her which only earned him a shove. Ruby shut the door locking the Impala only to smile as Stefan appeared in front of her. She hugged the younger vampire gently and walked with him inside. Damon frowned not used to the cold shoulder from Ruby, but knew he deserved it after he had hurt her yesterday. He followed them inside shutting the front door behind him and sighed softly.

"To be quite honest, I wasn't actually expecting to see you today after everything that had happened last night." Stefan admitted as Ruby poured herself a drink.

"Yeah I kind of figured that, but I don't know, despite it all I just had to make sure you guys were okay." She shrugged her shoulders slightly and took a sip of her drink.

Damon entered the parlor and shook his head as he stole her drink, "We're still standing aren't we?"

"So it seems. How are you, really?" She questioned the older Salvatore brother as she snatched her drink back and sat down on the couch.

He smiled sarcastically at the blonde as he flopped down beside her on the couch, "Just peachy, thanks."

It was just then when he noticed it and his sarcastic smile faded away. It was hardly noticeable, but it was there. The slight flinch, the slight involuntary widening of the eyes, he knew all the signs to look for, but he had never expected to see them displayed by her as she looked at him. It hit him like a ton of bricks and he almost felt worse than he did when he held Katherine's corpse in his arms last night. No, scratch that, he definitely felt worse than that. Ruby, his best friend, feared him and it felt as if he were getting simultaneously staked by millions of silver tipped vervain laced wooden stakes. It was the worst feeling in the world and then some.

Damon gently brushed back a lock of her blonde hair away from her face and sighed softly, "Ruby.."

"Don't. I..I just came by to make sure you guys were okay before I left Mystic Falls." She spoke softly as she took another sip of her drink.

His pale cerulean eyes widened as he sat up straighter not taking his attention off of her, "Leaving? So that's it? You kill Katherine and then it's bye Damon, see you next time I need a quick lay. Oh no, I forgot, you have Dean Winchester for that although I doubt he can quite measure up to me."

"You have seriously gone too far this time, Damon." Ruby slapped him across the face and then downed the rest of her drink.

The older Salvatore brother rubbed the side of his face and narrowed his eyes at the blonde demon, "I'm the one that went too far? You're the one who burnt her body, Ruby."

"Seriously? That is what this is all about? Damon, you shook me like a rag doll and threw me at a wall like I weighed nothing. I get that you were upset over her death, but don't you forget that she is the one that was roaming around free all these years while you falsely believed that she was entombed beneath that old church. She didn't care about you at all, Damon, why can't you see that? You and Stefan were just her little puppets to play with until she got bored and moved onto new ones. I was the one that was by your side when you and Stefan became vampires. I've been by your sides all these years and this is the thanks you give me? God Damon, she was going to kill my friends, hell, she was going to kill me and torture you two for all of eternity. Is that what you really wanted? For her to live and for me to die? Cause just say the word and I'm sure that pretty little demon killing knife of mine could find a nice resting place in my heart." She snapped as she stood up and glared at the raven haired vampire.

"Whoa, Ruby, calm down alright? Neither of us want you dead, okay? I think we all just need to take a deep breath and act rationally." Stefan spoke up trying to be the voice of reason.

Unfortunately for him, He hadn't anticipated on Ruby and Damon's fight going from verbal to physical in a matter of seconds. They tumbled around the room for a bit before Damon got her pinned to the floor. His pale cerulean eyes became crimson red as his fangs slid out into place and he hovered over the blonde staring down at her. Ruby's chest heaved as she breathed heavily and she caught both of the Salvatore brothers by surprise as she just stared up at Damon's face which was now in its vampiric form. She brought her hand up slowly and stroked the side of his face gently.

"I'm sorry, Damon. I know you loved her and I know it couldn't of been easy having me hate her for all these years. I hated her because she killed my mother. I hated her for the way she treated you guys, but most of all I hated her for hurting you. What was I supposed to do? Tell me, Damon, what the hell was I supposed to do? Let her kill me just so she can torture everything I've ever cared about for all of eternity? I'm so sorry, but I couldn't do that. You know me, Damon. I would of died fighting her if it meant protecting you guys and the Winchesters." Her voice cracked slightly as she stared up at him with tear filled eyes.

His face softened though still in vampiric form as he wiped away her stray tears gently with his thumb, "I know. I just..all this time I believed that I'd be reunited with her one day, you know? Then I found out she wasn't in that tomb after all. As much as I hated her for that, part of me was relieved to know that she was alive. That was all that mattered until she showed up here. As cruel and as evil as she was, I still loved her. I could of just left that orphanage with her, but I didn't. You killed her, but I was the one that held her there. I let you kill her and I barely even tried to stop you. What kind of monster does that make me?"

"Don't say that, Damon. You're not a monster. I know Stefan has said for years now that there is no humanity left in you, but he was wrong. You loved Katherine and you could of ran to safety with her. But you didn't. You just held here there in place and pleaded with me not to kill her even though you knew deep down inside that pleading with me wasn't going to work. You loved her, but your humanity was what kept you from saving her. Damon, even if you had gotten away with her, you knew deep down inside that she wouldn't of stayed away from us for long. As much as you loved Katherine, you let me kill her because you knew it was the right thing to do." Ruby spoke softly staring up at Damon unafraid of his vampiric appearance.

A sudden feminine gasp caught them by surprise and Damon's head snapped up only to see Elena standing a few feet away in shock obviously misunderstanding the situation. His fangs disappeared and his eyes transitioned back into their natural pale blue state. He looked just like his handsome self again. Damon stood up helping Ruby to her feet and stared over at Elena. He knew deep down that Ruby had been right, but it still hurt to see Elena right now considering she was practically identical in appearance to Katherine. The blue eyed elder Salvatore brother kissed Ruby's head softly and then disappeared in the blink of an eye running to who knows where. It was then that Ruby noticed that Sam was there as well and then she glanced around only to not see Dean anywhere in the room.

"What are you guys doing here? Where's Dean?" She questioned looking over at Sam although part of her cringed already knowing the answer.

"Cas went off to do angel stuff so I hitched a ride with Elena. She wanted to see her boyfriend and I just wanted to make sure you were okay. Dean? Oh uh, he stayed behind." The tall shaggy haired brunette explained as he rubbed the back of his neck nervously.

Elena was by now standing beside Stefan with her arms wrapped around his waist as one of his arms was draped around her and she rolled her eyes, "Oh please, Sam, he didn't just stay behind. He's locked in Aunt Jenna's bedroom with her and they are being loud."

Sam and Elena both cringed in disgust at the thought. Ruby, on the other hand, calmly walked over to the wet bar and poured herself another glass of whiskey. She handed Sam the keys to the Impala and headed upstairs only to find Damon in his room. The blonde demon entered the bedroom pushing the door shut with her foot and locking it before walking over to Damon who was currently sitting on his bed. She took a sip of her drink before handing it to him and sat down beside him. They took turns taking sips of the drink and then he set aside the now empty glass. They kicked their shoes off and laid down in his bed without saying a word.

Damon draped the blanket over both of them wrapping his arm around her as he broke the silence, "How did you know I was up here?"

"Actually I didn't know you were up here. I just wanted to get drunk without being under their judgmental stares and I knew you had a few bottles hidden up here." She explained with a shrug of her shoulders and held up a bottle of whiskey she had grabbed just prior to getting into the bed with him.

He opened the bottle for her taking a sip before handing it back to her and chuckling sarcastically, "Oh I see. You're only friends with me for the free booze."

"Yes, you finally figured me out. I'm only in it for the free booze. Oh and for your ridiculously hot body of course." She remarked seriously and then burst into a fit of giggles.

_Dear Diary,_

_Everything is so screwed up right now. Katherine's dead, for real this time, courtesy of me and Damon is totally heartbroken about it. Not that I didn't expect that. Damon and I fought about it although I think we're alright for now. I'm still a bit scared of him, but I'm toughing it out so to speak. Oh and here's the kicker, Dean slept with Elena's Aunt Jenna. Can you believe that? Not that I'm surprised. I kind of figured that would end up happening when I saw him flirting with her this morning. With the way he was acting before I borrowed the Impala, I just thought that maybe..nevermind. Who am I kidding? It's Dean Winchester. He'd screw anything with boobs. Then again so would Damon. Guys are such pigs! God, I sound like such a teenage girl. Maybe I should cut back on the free booze. Nah, what fun would that be? Well, I got to go. Damon just broke out the tequila. Full of surprises, that one._

_Ciao Bitch,_

_Ruby xx_


	9. Chapter 9

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Nine:

Damon and Ruby finally ventured back downstairs the following afternoon only to find Stefan in the living room with his girlfriend along with the Winchesters. The blonde demon smiled brightly upon seeing the tall shaggy haired brunette and proceeded to flop down beside him on the couch. She had no idea what any of them had been talking about, but then again she didn't really care. An awkward silence seemingly fell over the room until finally Ruby rolled her bright blue eyes scoffing slightly as everyone seemingly looked between her and Damon.

"Not that it's any of your business, but Damon and I didn't sleep together yesterday nor did we last night." She commented not looking anyone in particular in the room although she did notice Damon roll his own pale blue eyes.

The elder Winchester brother scoffed letting a sarcastic chuckle escape past his full pouty lips, "No, I'm sure he probably kept you up all night. Right Rubes?"

"You mean like you kept Elena's Aunt Jenna up all night? Oh wait, that's right, you don't have that kind of stamina that can keep a girl going all night long." Ruby retorted with a smirk and flipped her long blonde hair over her shoulder.

Dean laughed slightly and then glared over at the blonde demon, "Oh please! I have more stamina in my pinky than Damon ever had throughout his whole undead body. What? I never slept with Jenna. She made me go for a walk to calm down because some blonde demonic bitch stole my car. If anyone slept with Jenna, it was probably her boyfriend."

"You want your damn car back? Here, take your damn car and shove it!" She snapped after snaking the keys out of Sam's pocket and walked over to the front door opening it before throwing the keys to the Impala out into the pouring rain.

His green eyes hardened as he followed her over to the door and stared out into the rain not seeing his keys anywhere, "What the hell is the matter with you? Ate too many bowls of bitchy flakes this morning?"

"I told you. Don't call me that." Ruby responded in a lethally calm tone of voice before shoving Dean out into the pouring rain.

Unfortunately for her, She didn't notice the tall younger Winchester brother approaching her from behind and before she knew it she was out in the rain as well. Sam shut the door locking it before turning around only to see the two vampire brothers and Elena looking at him. He shrugged his shoulders and sat back down in the living room as if what they had all just witnessed was nothing new to them. Damon, however, was tempted to go outside, but he also knew better than to tempt fate where Ruby's wrath was concerned.

He inhaled the scent of his whiskey and then took a sip before looking over at Sam, "Maybe one of us should keep an eye on them."

"You could if you want, but I wouldn't bother. It's not the first time that they've gotten like this and I'm pretty damn sure it won't be the last time either." Sam remarked nonchalantly not feeling too worried about the pair outside in the rain knowing he'd check on them himself in a few minutes anyway.

Back outside Ruby finally gave up on trying to beat the door in and turned around only to be amused at the sight of Dean in the pouring rain trying to find his car keys. She sighed inwardly after a few minutes and stepped out from under the awning instantly getting soaked from the rain. She stopped a few feet away from where Dean was currently looking and bent down picking up the keys. Standing up straight, Ruby walked over to Dean and tapped him on the shoulder.

"You know, you are so totally hopeless without me." She held up the keys in question and her lips twisted into an amused smirk as he turned around to face her.

Dean snatched the keys from her and placed them safely in his pocket, "Only in your fantasies, sweetheart."

"Hah! Out of all the guys in the world, what makes you think I waste my time fantasizing about you?" The blonde demon laughed as she leaned against the front of the Impala with her arms folded across her chest.

His full pouty lips twisted into a sexy smirk as he approached her getting so close that their noses were almost touching, "Because I know you, Ruby. There's no one in this world that gets under your skin quite like I do and there is no one that gets under my skin quite like you do. If you really wanted anyone other than me, you wouldn't of gotten so upset over the thought of me possibly sleeping with Jenna. You can sleep with Damon all you want, but deep down inside you know that it's true."

"I..I don't want you." She lied as she felt herself involuntarily lean back against the hood of the Impala.

Their clothes soaked from the pouring rain clung tightly to their toned bodies as their eyes locked on one another. Her breath hitched in her throat as he brushed away a few stray strands of her now wet blonde hair from her face and his rough fingertips brushed against her pale yet damp skin gently. As much as she tried to deny it, the igniting passion in the fiery depths of her darkening blue eyes always seemed to give her away whenever he was this physically close to her. The rain had slowed down considerably and neither of them had even considered the fact that either of the vampires inside could be eavesdropping on their conversation. Of course with their stoic faces, It was hard to tell if they had been eavesdropping and had therefore been as shocked as Ruby currently was courtesy of the words that had just slipped out of Dean's mouth.

"_Marry Me_"


	10. Chapter 10

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers. "Love Story" belongs to Taylor Swift.

Chapter Ten:

_You'll pick out a white dress_

_It's a love story_

_baby just say yes_

_-"Love Story" by Taylor Swift_

Most girls dream about that one special day when they are the center of attention in a beautiful white gown walking down the aisle to the man that they love. It's envisioned as being the happiest most romantic day of their lives. Ruby, however, had never been like most girls. She personally loathed wearing dresses and only wore them on the most rarest of occasions. Yet here she was staring up at Dean Winchester with her back pressed against the hood of his beloved Impala. Their clothes were soaked thoroughly and clung tightly to their bodies as the rain continued to fall. He was gazing down into her bright blue eyes expectantly as he awaited her answer to the stunning proposal that he had just given her.

"Dean.." She trailed off unable to come up with the right words to say even though deep down inside she knew that he would be perfectly happy with just a one word answer to his proposal.

He pressed his lips to hers softly and then pulled back slowly, "I..I love you, Ruby. I know that seems completely out of left field right now, but it's true. We're probably one of the most unlikely pairs out there and yet somehow we're still drawn to each other..."

"Dean, I..I just don't know what to say. This whole thing is completely out of left field. I..I don't know anything about being a fiancée or a wife." The blonde demon interrupted the elder Winchester brother feeling even more stunned than before.

He simply nodded his head and stepped back giving her the opportunity to sit up. Ruby bit her lip and walked back toward the front door of the boarding house. As she got near the front door, she couldn't help thinking over everything that had just happened. Ruby reached out to grab the door handle only to pull her hand back rather quickly when realization finally hit her. She wasn't truly Ruby without Dean. Sure, being her best friend enabled Damon with the ability to bring out the best of Ruby's qualities yet it just wasn't the same. Dean just had this way of pushing her to the absolute brink and making her feel those god awful butterflies fluttering around in the pit of her stomach all at the same time.

"Dean!" The slender blonde called out before turning around only to be relieved when she saw that he was still there.

Their eyes met and for a moment it was as if everything had slowed to a stop around them. After that moment passed, Ruby surprised Dean by running toward him and leaping up into his arms. He caught her as she wrapped her legs around his waist tightly and held her there staring into her eyes in amazement. She brushed her fingertips against his cheekbones lightly before pulling him into a kiss. He returned the kiss holding her tightly against him almost as if he were afraid that he'd lose her if he were to let her go. Her hands slowly slid past his shoulders allowing her arms to drape around his neck as their kiss deepened.

"Yes." She said breathlessly as she broke the kiss to catch her breath although their lips were barely more than an inch apart.

He stared at her blankly for a moment and then his eyes widened as what she said had began to sink in, "Yes? Did you just say yes?"

"Yeah Dean, I did. Yes, I will marry you, shortbus." Ruby grinned slightly and then laughed softly as he spun her around in the rain.

Dean stopped spinning her after a moment and pulled her into a soft kiss, "God, I love you, Rubes."

"I love you too, Dean." She smiled against his lips deepening the kiss roughly as he carried her around to the side of the Impala.

He pulled the car door open and set her down on the backseat before climbing into the car himself. Shutting the door behind him, Dean locked the doors before hovering over Ruby. Her lips twisted into a smirk as she pulled her wet t shirt over her head letting it fall to the floor. His full pouty lips twisted into a sexy smirk as he admired the blonde beneath him for a moment and then pulled his own wet t shirt over his head. When Sam finally unlocked the front door poking his head outside, the rain was barely more than a light mist and he unfortunately didn't see the quarrelsome pair anywhere. The Impala was still parked where he last saw it so he ventured toward it only to find once he got there that the windows were fogged up. It didn't take him long to figure out what was going on inside of the classic car and he jumped slightly startled as Ruby's hand smacked against the fogged up back window before sliding downward. He wrinkled his nose in disgust although he was happy that they had made up. Shaking his head, Sam ran back inside shutting the front door behind him only to see the Salvatore brothers and Elena Gilbert looking at him.

Elena, ever the curious yet caring one, spoke up first wondering what Sam had found out there, "So are they alright or did they kill each other?"

"They are fine. Actually they are more than fine and I wouldn't go anywhere near the Impala anytime soon if I were any of you. Consider yourselves warned." He remarked with a slight chuckle and sat back down in the living room.

Damon furrowed his eyebrows for a moment before picking up his glass of whiskey, "Well brain stabbing imagery aside, thanks for the warning."

He flashed a sarcastic grin in Sam's direction before running upstairs to his room in the blink of an eye courtesy of his vampiric speed. Taking a sip of his drink, he sighed softly and shook his head as he turned around only to see her approaching the doorway of his room. Damon scoffed slightly and took another sip of his drink as the young brunette stepped into his room.

Elena eyed him with a glimmer of concern in her doe like brown eyes though otherwise she remained stoic, "You love her don't you, Damon?"

He shrugged his shoulders nonchalantly and raised his eyebrows at the brunette, "Didn't we already discuss this a while ago?"

She scoffed and shook her head lightly, "I'm talking about Ruby. You love her don't you?"

Damon shrugged his shoulders again and took yet another sip of his drink before appearing right in front of Elena shutting the door behind her, "Yeah, so? She's my best friend. I think the real question here is do you love Stefan as much as you say that you do?"

Elena gulped as her chocolate brown eyes became locked in a gaze with his pale cerulean eyes finding it hard to look away. She knew that she wasn't being compelled though because of the vervain necklace she was currently wearing which was a relief and yet the effect he still managed to have on her despite the vervain was quite discomforting. Their lips were just about to meet when the sound of her cell phone ringing broke them apart.

Seeing that it was a text from her brother, Elena sent one back to him before looking at Damon, "I should probably go. Uncle Jonathon is here and I promised Jer that I wouldn't let him face our uncle alone."

Damon nodded his head holding the door open for her and watched her walk out of his room, "Always a pleasure, Elena."

He shut the door once she was out of view and downed the rest of his drink unaware of the danger that Elena's uncle would bring to the vampires of Mystic falls. Meanwhile downstairs in the cellar, the door inside opened revealing the secret Salvatore vervain garden. A figure wearing a grayish hooded cloak stuffed as much of the vervain as it would fit into a bag. When no more would fit, what was left of the garden burst into flames. Damon, Stefan, and Sam all arrived at the same in front of the cellar only to find the door open. Sam had grabbed the fire extinguisher on the way down as they had all smelt the smoke from the flames. With the shiny red canister in hand, Sam approached the open door to what was once the secret vervain garden and shot a blast of the canister's foamy white contents. He kept spraying the flames until they were gone. It was Stefan who realized that what was burnt had been less than what had actually been in here. Despite their advanced senses, neither Salvatore could pick up on the trace of any scent left behind by the arsonist. It was Sam, however, who surprised them by grasping his head as his eyes squeezed shut trying to fight against the obviously immense amount of pain. Both vampire brothers tried to help him and it was only after a few moments that he was back to normal so to speak.

Damon exchanged a look with Stefan before glancing over at Sam, "What the hell just happened?"

"I..I really don't know. I just took a step toward you guys and it was as if I had walked right into a damn psychic vision." He remarked sitting down and catching his breath.

"You sound like you've had them before." Stefan commented and then glanced at Damon.

"Uh, yeah, I got them for a while, but they stopped after Dean killed the demon that poisoned me with the demon blood in the first place." Sam explained glancing at both of the brothers.

Damon paced around for a moment before looking at the taller Winchester brother, "Is it possible that whoever burned the garden left behind a psychic trace and you were the only able to pick up on it because of your previous experience with visions?"

"Uh, I don't know. Yeah I guess it's possible. I didn't see much though. There was this wooden box and when it opened it revealed this mechanism. You have to insert something into it and the mechanism moves. There was also fireworks and Damon." Sam explained taking the brothers through what he had seen during that brief vision.

His pale cerulean eyes widened and he glared slightly at Sam, "What do you mean there was me? What was I doing? Who was I doing?"

"You were dead. Well, for real dead. There was a stake protruding from your chest and you were on the floor in some room. I saw a wooden stairwell and flames. There was someone there at the top of the staircase, but I couldn't make out who it was that was standing there." He continued before Stefan led him back to the living room and handed him a drink.


	11. Chapter 11

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Eleven:

Showered and now in dry clothes, Dean and Ruby were all smiles until they entered the living room of the Salvatore boarding house. The look in Sam's deep green puppy dog eyes said it all. They both went to his side to ensure that he was okay although Ruby also glanced over at Stefan who seemed to be in a rather brooding like state. Damon, of course, was nowhere to be found and the blonde demon was beginning to wonder if something had happened to him only for Stefan to speak up relieving her from thinking the worst.

"Someone burnt the garden in the cellar, but it was only about half full. Whoever it was also left behind a psychic trace that, uh, Sam picked up on." The younger Salvatore brother explained to Dean and Ruby rather calmly.

Dean glanced at Sam and then looked at Stefan in disbelief, "What do you mean Sam picked up on it? Wait, a garden? Someone burnt down your garden and you're all upset?"

"It wasn't just any garden, Dean. It was a garden of vervain. It's a herb that's toxic to vampires if ingested. Humans that wear or ingest it can't be compelled by vampires either. Wait, Stefan, what do you mean Sam picked up on a psychic trace?" She smacked Dean's arm explaining the garden to him before turning her attention toward the younger Salvatore brother.

"I put out the fire with the fire extinguisher and then we were looking around for clues. I turned around so that my back was facing the little garden room and walked toward the Salvatore brothers. I only took about a step and then I was hit with a psychic vision. I saw some kind of small wooden box with a mechanism inside of it. There was also fireworks and Damon was on the floor with a wooden stake in his chest. It was in a room with a wooden staircase. There was also flames and someone was at the top of the staircase, but I couldn't tell who was standing there." Sam cut in explaining what he saw and sighed softly.

His green eyes widened as he listened to what his brother said and then he looked at Stefan, "Who knows about this vervain garden that you had?"

"Well aside from the four of us and Damon, Elena also knows. So does Caroline. Our Uncle also knew about it, but he's dead so as far as I know he never told anyone." He furrowed his eyebrows in deep thought as he tried to think of anyone else who could of possibly of known about the garden.

"Alright, we need to check with Elena and Caroline to make sure they didn't tell anyone about the vervain garden. Hey Sammy? Do you think you could sketch out that box you saw in your vision with the mechanism inside of it? If we had a better idea of what it looked like, it might help us figure out how it's connected to the fire." Ruby explained looking at Sam who simply nodded at her in agreement.

With that said, Sam got to work on his sketch while Stefan agreed to run over to Elena's as Ruby had agreed to go find Caroline, but of course no one wanted her to go alone. She watched as Dean somehow goaded Damon into a round of Rock, Paper, Scissors. Ruby knew this was pointless since Dean always chose scissors and true to form, he chose scissors yet again while Damon's pale hand remained in the formation of a fist. A smug expression formed on Damon's face much to the annoyance of Dean and the elder Winchester brother pulled Ruby into a kiss before reluctantly releasing her to the vampire.

His green eyes hardened into a glare which he targeted on Damon, "Don't even think about touching my fiancée or I'll stake your sorry ass so fast you won't even see it coming."

"Your what?" Stefan and Sam exclaimed simultaneously as they looked over at Ruby in shock.

"Um, surprise?" She shrugged her shoulders and smiled softly.

"Congratulations to the both of you." Stefan nodded his head shaking Dean's hand before hugging Ruby.

"Well it's about damn time! Welcome to the family, Sis." Sam grinned softly pausing from his sketching duties long enough to pull Ruby into a hug spinning her around slightly before placing her back down on her feet.

Though she'd probably never admit it out loud, Ruby couldn't help feeling touched by Sam's reaction and the fact that he had called her 'Sis'. She watched the Winchesters do the whole brotherly hug thing and smiled proudly at them. Before she could say anything, however, Damon grabbed her arm and whisked her out of the house using his vampiric speed. He finally stopped running when they had reached The Mystic Grill and pinned her under his pale cerulean stare against the brick wall around the corner from the entrance.

"I'm a demon, remember? You can't compel me, Damon." She remarked calmly as she returned his gaze.

Damon looked at her in disbelief and shook his head, "I'm not trying to compel you, Ruby."

"Then what are you trying to do?" The newly engaged blonde questioned the handsome vampire.

His lips twisted into a slight smirk as he gazed down at her, "Just checking to ensure you haven't lost your damn mind. A hunter, Ruby? Why would you want to marry him?"

"Because, Mr. Salvatore, I love him." She smiled softly not realizing the significance of what she had just said and pushed past him making her way into The Mystic Grill.

_**The horse drawn carriage pulled up to the Salvatore boarding house and she smiled when she saw Stefan Salvatore waiting there for her. With her blonde locks pinned back into a fancy up do and her new crimson red corseted dress, Ruby Covington looked like a poster girl for southern belles. Stefan helped her out of the carriage and she promptly greeted him with a hug. The carriage pulled away and a knowing smile appeared on the younger Salvatore brother's face which only seemed to make Ruby even more curious. Hearing footsteps, the blonde turned around only to see the older Salvatore brother, Damon, standing a few feet away from her in his uniform. A grin spread across her face as she hiked up her dress running toward him and let it go at the last second leaping up into his arms.**_

_**"But how..I mean..I thought you were off fighting in the war?" She asked as she pulled away slightly cupping his face in her hands and staring into his pale cerulean eyes.**_

_**Damon grinned softly obviously amused by her reaction and chuckled slightly, "I was, but I realized that I didn't belong there. I belong here with my family and with you. Father is royally miffed though. He'll get over it eventually."**_

_**"Well, regardless, I am still so very proud of you." Ruby smiled as he set her down on her feet.**_

_**He and Stefan shared a knowing look before he dropped down on one knee in front of the blonde, "Proud enough to marry me?"**_

_**"What? I..Of course I'll marry you, Damon." She grinned happily as her bright blue eyes sparkled with joyous tears.**_

_**Damon grinned sliding the silver ring onto her left ring finger and stood up pulling her into a kiss. The silver banded ring had a rather simple design of a six leaved ruby flower with four diamond leaves on either side. In the center of the ruby flower was a ruby bud encircled by silver and diamonds. Once the newly engaged couple pulled apart, Stefan grinned softly congratulating his brother and his soon to be sister in law. The sound of someone clearing their throat caught their attention and they turned only to see that it was the father of the Salvatore brothers. Naturally, Ruby was the first to speak up. After all, she always did have a way with the Salvatore men.**_

_**"Giuseppe, how wonderful to see you! How are you and Lady Salvatore faring today?" The newly engaged blonde walked over to her soon to be father in law and curtsied in front of him before he kissed the back of her hand as was proper in those days.**_

_**He let go of his hand smiling at the blonde and eyed his sons, "Very well although we'd be better off if our oldest hadn't of shamed us like he did. What is the meaning of this ring? Ruby, did you finally find yourself a proper suitor?"**_

_**"Shamed? Damon made a very honorable choice. He chose his family. Oh, that. Well, I'm sure you'll find out soon enough anyway so I might as well tell you, Giuseppe. Your oldest just asked for my hand in marriage and I accepted." She glanced over at Damon and grinned softly.**_

_**Giuseppe Salvatore, though he adored Ruby most of the time, didn't appear too fond of her announcement, "Damon? Why on earth would you want to marry him? Why not Stefan?"**_

_**"Because, Mr. Salvatore, I love him." With that said, Ruby took Damon's hand and walked past his father making their way into the Salvatore boarding house.**_

Caroline was sitting at a table with Bonnie in The Mystic Grill when Ruby walked in. She ordered a Coke and sat down with the girls surprising them with her presence since they obviously weren't expecting her. Damon approached the table a few moments later quite amused by the small talk that Ruby was making with the two girls. She looked over at him for a moment only to roll her eyes at the smirk on his face. Of course that only made him smirk more as he watched her take a sip of her Coke.

He could tell that Ruby was about to say something so he spoke up instead, "You know, it's a good thing Elena left the boarding house when she did today. At least she didn't have to witness the flames billowing out of the cellar."

Pure shock was apparent on Caroline's face as she looked at both Damon and Ruby, "Flames? Oh my god, what happened?"

"Well I didn't actually see it, but someone set fire to the cellar of the boarding house. Thankfully no one was hurt since the boys put the flames out before it became out of control." She remarked sincerely because she truly was grateful that her boys hadn't gotten hurt.

Bonnie took a sip of her own soda and appeared sympathetic toward the two of them, "Well I'm glad no one got hurt. Why would someone set fire to a dusty old cellar anyway?"

"That's exactly what I thought! Luckily for the Salvatore brothers, there was only minimal damage from what I heard. It was only in one general location so I'm sure it won't take the boys long to figure out what caused the fire though, right Damon?" The older blonde took another sip of her Coke and batted her eyes slightly at the blue eyed vampire.

Damon eyed her for a moment before nodding his head in agreement, "Of course. Such a shame that one of Stefan's prized possessions got destroyed by the flames though. Sure, it was a bit too kitschy for my taste, but my brother adored it."

"Yeah exactly. Well, uh, it was lovely chatting with you girls, but we should probably make sure the boarding house didn't get even more wrecked while we were gone." Ruby simply said before practically dragging Damon out of The Mystic Grill.

It wasn't until they returned to the Salvatore boarding house that Damon and Ruby found out from Stefan that Elena hadn't told anyone about the secret vervain garden in the cellar. They were seemingly back at square one as Ruby poured herself a drink and then Damon snapped his fingers before running off. He returned mere moments later with a beige flyer in his hand showing it to Sam, Dean, Ruby and Stefan. The vision that Sam had in the cellar was beginning to make sense to them and it was almost as if a light bulb had gone on above Ruby's head.

"The fireworks in Sam's vision, that's it! Whoever stakes Damon is going to stake him on the night of the Founder's Day celebration which according to this flyer is tomorrow night. Wait, you guys said that whoever set that fire in the cellar took a lot of the vervain from it right? Well, what if the vervain is to subdue Damon? I mean, they have to weaken him somehow right?" Ruby asked taking a sip of her drink before looking over at Stefan.

"She has a point. Sam, think back to your vision. Specifically when you saw someone at the top of the stairs. Now I know you said that you couldn't tell who it was that was standing there, but can you make out anything about them at all?" The younger Salvatore brother instructed the younger Winchester brother hoping it might give them some kind of lead to work on.

"Well everything is a bit hazy from the smoke and flames. I can see the person standing at the top of the stairs though. It's a girl from what I can tell, but nothing is really standing out about her." Sam remarked with his eyes closed and then opened them only to see Ruby's eyes flash to their angrier onyx shade.

"Oh my god, It's Bonnie! What? You heard her, Damon. She referred to the cellar as being a dusty old cellar. Now how would she know that unless she's been down there herself?" She stated as her eyes returned to their normal bright blue shade.

Damon eyed her for a moment and then shook his head, "Maybe because it's a cellar, Ruby."

"Yeah I know that, Damon, but she knew you were lying when you said that one of Stefan's prized possessions was burnt in the fire. I could see it in her eyes. Caroline totally believed you, but not Bonnie. Also she had a tiny sprig of vervain caught in the cuff of her jacket." The blonde demon explained with a smug 'I know I'm right' look upon her face.

He rolled her eyes at her and then smirked softly, "Fine, you're right, but that still doesn't help keep me away from that stake tomorrow night. I can't believe I'm about to say this, but we need a plan."


	12. Chapter 12

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Twelve:

Elena smiled slightly as she approached the Winchester brothers and Ruby with Stefan, "Alright, the mayor is speaking now and the founding families are on stage. So we have approximately fifteen minutes before they start the fireworks. Wait, where's Damon?"

"He saw something and ran off before we could stop him. Ruby wanted to follow, but we figured it would be safer if we waited for you guys." Sam explained as his soon to be sister in law practically fumed beside him.

"Dammit. Well, I think we figured out how Damon ends up staked. That box with a mechanism you saw in that vision? It was originally part of a music box. At the time, the founding fathers were gathering whatever they could to defeat the vampires and to track them. Father donated mother's music box, but I don't know exactly how that mechanism from inside it could affect the vampires." Stefan explained and then glanced around in search of his older brother.

Dean squeezed Ruby's hand reassuringly and glanced around himself, "Well we need to find it and..we need to find Damon also."

"You're right. Elena, you and Stefan head back over toward the stage area. Dean, you search the square and Sam will help me search the stores." Ruby instructed squeezing Dean's hand in return before linking her arm with Sam's arm.

He looked at his fiancée and shook his head, "Why does Sam get to help you? I'm the one marrying you, woman."

"First of all, don't call me woman and second of all, he's taller. Now be careful." She shrugged her shoulders speaking as if it were the most obvious thing in the world and walked off with Sam.

Damon, however, had entered the building where Elena's father had practiced medicine before he passed away and wasn't surprised to find Elena's uncle Jonathon Gilbert there. He also wasn't surprised when John pulled out the boxed mechanism from the inner pocket of his black suit jacket. He discreetly sent a text to Ruby before running toward John knocking the elder Gilbert off of his feet. Unfortunately for him, John was prepared for that and he pulled out a wooden stake stabbing Damon right in the side. John stood up dusting himself off and shook his head as he picked up the wooden box containing the mechanism.

"It's all over, Damon, but don't worry. If that beautiful blonde of yours turns out to not be a vampire, I'll spare her life. I'm sure I can find some use for her. Maybe." His lips twisted into a sinister smirk as he opened the box revealing the mechanism.

Damon fumed at the thought of John going anywhere near Ruby and clenched his fists as he got to his feet now healed, "Stay away from her, you son of a bitch!"

"Ah ah ah, don't use that tone with me. I'll do whatever I want with her, Damon. Who's going to stop me? You?" He laughed and turned the key to the mechanism.

He began to lunge at him only to fall to the ground grasping at his head in pain as a high pitched sound began to flood the area at a loud volume. Of course not everyone could hear it. Only the vampires that were in a certain amount of distance from the mechanism or at least that's what John thought. Stefan grasped his head in pain as the high pitched sound reached him and dropped to his knees. Elena tried to help him although she didn't know what was hurting him and was relieved when Dean showed up. With the local cops sticking every vampire with vervain, Dean helped Elena get Stefan out of sight unaware of the exact danger Ruby and Sam were in. The two of them were walking toward the late Grayson Gilbert's clinic when the high pitched sound hit them as well. They both grasped their heads in pain although it hurt Ruby more since she actually was a demon and Sam only had demon blood in them. Cops approached them injecting them both with vervain unaware that it would have little to no effect on the pair. John smirked as he knelt down injecting Damon with vervain. He stood back up turning off the mechanism which was the last thing Damon saw before everything went black.

"Wait, wait, it stopped. I..I think I'm okay." Stefan remarked breathing heavily as Elena brushed his hair away from his eyes gently.

Dean glanced around before looking down at the younger Salvatore brother, "What the hell just happened?"

"The..the mechanism. They must of figured out how to configure it so that it let out this high pitched noise that only vampires can hear. Makes it a hell of a lot easier to narrow down which one of us is a vampire and which aren't vampires." Stefan explained as he sat up straighter and regained his composure.

Elena helped him to his feet and the three of them headed into the town square walking as normal as possible, "Wait, where are Sam and Ruby? Do you think they found Damon?"

"I don't know. Elena, I need you to concentrate for me, okay? Think really hard. Is there a basement anywhere around here with a wooden staircase?" He asked gazing at his girlfriend reassuringly.

The young brunette glanced around before looking at both of the older men before her, "The only one I know of is the one in dad's clinic. Come on, there's another way in besides the front."

As Elena led them to the side entrance of the clinic, Damon lay on the cold concrete floor of the clinic's basement. His pale cerulean eyes opened slowly only to catch a glimpse of her long blonde hair. He tried to reach out toward her, but he couldn't. The younger Winchester brother groaned softly as he came to and glanced around only to see an older man standing over Damon's body. Unaware that he was being watched, Jonathon Gilbert pulled out a wooden stake and smirked at the dark haired vampire laying on the ground before him. He raised the stake up and was about to plunge it down into Damon's heart when a large hand wrapped around his wrist stopping him. Sam knocked the stake out of the older man's hands and they fought before John managed to get a cheap shot in. Running toward the stairs, John lit his lighter and tossed it causing a fire to break out. Sam began to help Damon only for the vampire to point toward the unconscious blonde demon.

"Ruby! C'mon Rubes, wake up! Dammit!" Sam brushed her blonde locks away from her face and scooped her up into his arms.

The fire grew unfortunately and as the trio reached the side entrance, they came face to face with Bonnie. The young witch wouldn't let any of them enter the clinic and Dean was about to force his way in there when Stefan stopped him. The younger vampire knew that Elena was their best chance at getting Bonnie to let them through so he let the girls talk it out.

Elena frowned at her so called best friend and sighed softly, "Bonnie, come on! I know you're still upset about your grandma's death. I don't blame you, but this isn't right."

Bonnie folded her arms across her chest and narrowed her brown eyes at Elena, "I'm doing Mystic Falls and the rest of the world a huge favor, Elena. Those vampires are nothing, but bad news. Sam, Ruby, Damon, and the rest of them are all getting what is coming to them."

Dean's eyes widened and he grew angry upon hearing their names, "Sam and Ruby are down there? You son of a bitch! They aren't vampires, you dumbass!"

The young witch looked at the elder Winchester brother in a mixture of surprise and confusion, "Then why did it affect them just like it affected the other vampires?"

"Ruby is a demon and Sam has demon blood in him. I doubt it affected Sam as much as it affected Ruby. Sam is just a regular human, Bonnie. Are you really just going to let him die down there?" Stefan questioned her as Elena tried to keep the peace amongst them.

Down in the basement, however, Sam coughed as the flames continued to surround them blocking their only way out. He turned only to see Castiel standing there and he had never quite been so happy to see the angel as he was now. The blue eyed angel touched their heads transporting them out where the side entrance was and then made his way over to Damon. He knew deep down inside that angels weren't meant to save creatures like Damon, but then again he also wasn't supposed to save creatures like Ruby either. Grabbing the vampire's shoulder, Castiel transported them both out of there just in time as the ceiling collapsed mere seconds later. Bonnie disappeared during all of the commotion leaving the rest of the little group to return to the Salvatore boarding house minus Elena who went home to ensure that her brother was safe. As Stefan tended to his older brother, Dean tended to Sam and Ruby with help from Castiel. The angel healed Sam's smoke inhalation which made the younger Winchester brother feel more at ease since he wasn't coughing anymore. He also healed the head wounds that both Sam and Ruby had sustained as a result of the cops having to subdue them in order to get them down into the basement.

It wasn't until the next morning, however, that both Sam and Damon were up moving around again. They all kept an eye on Ruby and even Elena ended up stopping by with food for the boys. Both of the Winchesters were in the guest room when Ruby's bright blue eyes finally opened slowly. Dean was sitting in a chair next to the bed appearing relieved at the sight of her awake. Sam, on the other hand, was sprawled out beside her on the bed sound asleep. His face almost resembling that of an innocent little boy as he slept.

"Wait, what happened? What about the plan?" She questioned feeling confused as the last thing she remembered was her head hurting from that excruciating noise.

Dean kissed her head softly and grasped her hand within his hand, "You and Sam got mistaken for vampires. Elena's jackass of a uncle nearly staked Damon, but Sam stopped him. They fought and the son of a bitch got away. He set fire to the basement before fleeing. If it wasn't for Cas, there's a good chance you three wouldn't be here right now. You were also right about Bonnie."

"Dammit. I knew it. Is everyone okay?" Ruby asked although she had a feeling that they were all okay anyway.

He nodded his head and smiled softly, "Yeah we're all fine. How are you feeling?"

Ruby waved him off as she felt sore, but wasn't about to let him know that. Before either of them could say anything further, however, Damon appeared in the doorway. She noticed the smear of blood on the collar of his white t shirt almost immediately and shook her head. It was something that she was used to considering he was a vampire after all, but something in those pale cerulean eyes of his told her that this time it was different. Realization hit her and her bright blue eyes widened considerably.

"Damon, what the hell did you do?" She asked as she sat up a bit not taking her eyes off of him.

He shrugged his shoulders and smirked smugly in a way that only he could, "What do you think I did, Ruby? I made sure that bastard couldn't hurt us."

"What about Elena?" Ruby questioned him knowing now exactly what he had done.

Damon shrugged his shoulders again and grinned softly, "Oh she was there. She's cute when she's pissed, but she understood why I had to do it."

"Ugh, you are impossible, you know that?" She smacked him upside the head with her pillow and turned over resting her head on Sam's shoulder as she snuggled into his side.

Damon walked toward the door only to smirk to himself, "I know. You wouldn't have me any other way."

His laughter echoed throughout the house as he walked out of the room and a pillow went sailing past him only to crash into the wall instead. Damon always did know just how to get to get under Ruby's skin.


	13. Chapter 13

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Thirteen:

It didn't take long for things to go back to normal or at least as close to normal as you can possibly get in a town like Mystic Falls. The Winchester brothers left town on a hunt though promising Ruby that they would be back for her. Of course what they failed to mention was that they were having Castiel check in on her from time to time. It was Damon who had discovered the angel's presence first. His fangs elongated and his eyes grew red right before he attacked the unsuspecting angel. The blonde demon who had been at the Mystic Grill with Elena and Caroline returned home to the Salvatore Boarding House just then unaware of what was going on inside. She was horrified to see Damon attacking the angel and her eyes transformed into deep onyx pools of anger as she kicked the vampire rather harshly in his side. His features softened when he saw that it was Ruby and he returned to his normal handsome appearance. Her eyes returned to their normal bright blue shade though she rolled them at the vampire before helping Castiel up. Convinced his healing powers weren't working fast enough, Ruby walked Castiel out of the study intent on patching him up.

"I am so sorry, Cas. Damon can just be such an idiot at times. Please don't tell the boys. Dean wouldn't hesitate in driving back here just to stake Damon." She pleaded with the angel not wanting to lose her best friend despite the fact that she was currently pissed off at the vampire.

Castiel looked at the blonde and nodded his head in agreement, "I won't tell them as long as you can promise me that he won't be harmful toward you."

"He won't, I swear. He never has and he never will." Ruby assured Castiel only to watch him vanish a moment later.

Consuming the blood of an angel had been a whole new experience for Damon and he was unsure that he even liked it. The blood tasted sweet yet tangy at the same time. It made his body feel tingly which he honestly thought was absolutely absurd. Damon sensed her presence before she even said a word and spun around grasping her wrist before her hand could make harsh contact with his head. Their blue eyes became locked in a heated gaze which she broke after a few moments when she roughly pulled her wrist out of his grasp.

"Damn it, Damon! When I told you not to hurt the Winchesters, Castiel was included in that." She fumed glaring at the dark haired vampire as her hand flew across his face smacking him harshly.

He remained stoic though his eyes softened as he watched her turn on her heel heading upstairs, "Ruby, wait!"

Using his vampiric super speed, Damon was upstairs in the blink of an eye cornering Ruby. She wanted to be mad at him for attacking her friend. She truly did, but his close proximity to her was making it hard for the blonde to focus. The blonde shoved him hard against the wall in the hallway and his lips twisted into a smirk before her lips crashed upon them. He ran them into his room slamming the door shut behind them intent on enjoying every moment he could with _his _Ruby. Damon's happiness was short lived, however, when the Winchesters returned two days later and the engaged couple resumed acting like rabbits so to speak. Though there was still no date set for the wedding, Elena and Caroline along with Elena's Aunt Jenna somehow managed to get Ruby to go dress shopping. It wasn't long until Ruby had found the perfect wedding gown. It was an off the shoulder gown made from a soft off white material. The dress hugged her curves perfectly and it was long enough to be considered a wedding gown while also being short enough for her to dance in if she were to dance after the wedding. Of course when it came time for her first fitting, Ruby decided she needed a male's opinion so the girls dragged Stefan and Sam along with them to the bridal shop.

"Can someone please come in here and zip my dress up for me?" She called out softly and smiled when Elena entered the dressing room.

The young brunette grasped the zipper and dragged it upward with a little bit of a struggle, "There. Zipper's acting weird though."

"This can't be my dress. I can hardly breathe in it. I feel like a damn stuffed sausage." Ruby complained as she stepped out of the dressing room so everyone else could see her.

"Ruby, not to sound rude, but you're practically spilling out of your dress." Sam remarked feeling rather uncomfortable discussing his soon to be sister in law's cleavage and watched as she stormed back toward the dressing room.

Elena followed Ruby back into the dressing room and unzipped the dress peeking at the tag, "It's the same size, Ruby."

It was only a few hours after Ruby begrudgingly agreed to have the dress taken out a bit that Damon found her asleep in his bed. Her nose was a bit red and he could see the salty tear stains running down her face which told him that she had obviously been crying. Shaking his head, he cursed Dean Winchester's name believing that Dean must of been behind Ruby's tears and entered his bathroom only to freeze in his tracks. There were numerous boxes of various brands scattered on the counter while numerous tell tale white sticks lay haphazardly in the sink. They all read positive and his eyes widened in realization. He glanced out at the sleeping blonde before looking at himself in the mirror running his fingers through his dark hair and sighing in frustration. Dean Winchester knocked Ruby up. He had gotten the ultimate checkmate and she would be his forever.

"Whatever you're up to, don't do it, Damon." Stefan spoke up sensing his brother's smirk as Damon entered the room.

Damon poured himself a drink and chuckled softly, "I'm not up to anything, Stefan. I just happen to know a really juicy secret involving Ruby."

"You never were one to divulge her secrets, Damon." The younger Salvatore brother remarked glancing up from his book only to look at his brother pointedly.

He smirked ignoring the Winchesters and took a long sip of his drink, "This is true, but that is before I found out that she is with child."

"What? And you think it is yours don't you?" Sam inquired shocked at the announcement yet looking at the older Salvatore brother knowingly.

Damon shrugged his shoulders only to grin softly, "Vampires can't procreate, but we sure love to try."


	14. Chapter 14

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Fourteen:

Dean wasn't surprised when Damon announced that Ruby was pregnant because the elder Winchester brother had already known. After all, he had been the one to purchase the various tests for Ruby and he had also been the one that had been kicked out of the room by the pregnant blonde once they both realized that she was indeed pregnant. He couldn't help eying the older Salvatore brother suspiciously as he had expected Damon to perhaps be a bit more upset over the news that Ruby was pregnant. It was almost as if there were something that Damon wasn't saying.

Damon could feel Dean's eyes burning a hole into him and smirked softly before turning to face the elder Winchester brother, "I slept with Ruby."

Dean, who was already standing up, walked over to Damon grabbing him by the collar of his shirt and slammed the vampire into a nearby wall, "What the hell are you talking about?"

The blue eyed vampire grimaced before looking right into Dean's eyes, "While you and Sam were off hunting ghouls and goblins, I pissed Ruby off and in turn, the girl simply couldn't keep her hands off me."

He made the mistake of letting go of Damon and as he threw a punch in the direction of the vampire's face, the vampire in question used his vampiric speed to move out of the way which resulted in Dean's fist colliding with the wall. Blood trickled along Dean's fist and the only thing that kept Damon from attacking him aside from Ruby of course was the fact that he was well aware that Dean's blood was laced with vervain courtesy of Stefan. His features softened as he sensed her appearance and turned only to be on the receiving end of a rather harsh glare from the pregnant blonde. She went to her fiancé's side and tried to lead him to another room so that she could tend to his fist. Dean refused though and gave her a look which made everything all too clear to Ruby.

"Dean, I'm sorry. It didn't mean anything, okay? It's not going to happen again." She assured him letting his hands rest on her still flat stomach.

He was still upset, but having his hands on her stomach visibly calmed him, "It may not of meant something to you, Ruby, but it obviously meant something to him."

As if on cue, Damon vanished and Ruby was left speechless. She snapped out of it after a few moments and excused herself before heading back upstairs. She didn't see Damon in his room so she snatched the keys to his car before heading back downstairs. Ruby informed Sam and Stefan where she was headed though simply only told Dean that she was going out as she needed some time away from both him and Damon. Walking outside, Ruby got into Damon's car and drove over to Elena's house. The brunette in question had left to see Stefan by the time that Ruby had arrived so the troubled blonde was a little surprised when Jenna opened the front door instead. The auburn haired beauty let her in and soon enough the two of them were sitting down at the table with bowls of ice cream.

Jenna looked at Ruby and smiled sympathetically at her, "Okay I can tell that you have something on your mind so what is it? Feel free to vent, Ruby, I'm a good listener."

"You know how the wedding dress didn't fit me right at the fitting? It's because I'm pregnant. Everything is just so crazy right now and my feelings are all over the damn place. I just don't know what to do." She admitted and sighed softly as she slid a spoonful of ice cream into her mouth.

She wasn't surprised by the pregnancy announcement and simply smiled again, "Well congratulations on the baby. If you need anything, just let me know. As far as these feelings of yours go, them being all over the place wouldn't happen to have anything to do with a certain blue eyed Salvatore would it?"

"Yes, but it's more than that, Jenna. It's complicated at best. I've known the Salvatores my whole life. I dated Damon and we were even engaged once. He knows me better than anyone and we've been on this friends with benefits kick for years now. Dean, well, we hated each other at first. Well, more like he hated me. I somehow became the big sister that his little brother Sam never had. I was like the thorn in Dean's side, you know, and then all the tension finally exploded between us in the back of his car one fateful night. I always kept the Winchesters and the Salvatores in the dark about each other. It was Damon that ruined that when he followed me to a bar one night and inadvertently found me talking to the Winchesters. Dean and Damon pretty much hated each other since. Sam and Stefan are like the little pain in the ass brothers that I never had. Dean, I know he loves me and I'm having his baby. At the same time though, he and I both know that Damon loves me too. I just don't know what to do. I'm torn and I hate it." Ruby vented practically all in one breath and looked at Jenna.

Jenna nodded her head letting her mind process all of that information and looked at the blonde, "You were right. That is complicated. Look, you can't let all of that stress you out especially now that you are carrying a baby. From what I understand, no matter what happens, you will always have Sam and Stefan in your life which is good. Now you just have to figure out where your heart truly lies. Is it with Dean or is it with Damon? So tell me. Why did you say yes when Damon proposed to you?"

"Because I loved him. He wasn't always like the way he is now. The Damon I fell in love with was sweet, caring, romantic, adored his little brother, and had a way of expressing just how he felt about a person with one look. I mean, even when he became the Damon that he is now, I still love him because deep down he is still Damon. Hell, I've changed too. I wasn't always this bitchy. I was actually a good girl once. Go figure." She remarked and shrugged her shoulders with a soft smile.

She smiled eating a spoonful of ice cream and then pointed the spoon at Ruby, "Alright then, So why did you say yes when Dean proposed to you?"

"Because I loved him. I never meant to fall for him, but I did. He has this tough exterior, but he's a good guy at heart. Family is everything to him. I mean, what girl wouldn't want a guy like him? Now I'm having his baby and he's mad because I slept with Damon. Oh, I didn't mention that did I? Damon ticked me off and we ended up in his bed. Ugh, I swear, they both drive me crazy!" Ruby huffed and ate some more of her ice cream unaware that Damon was listening in to their conversation.

He smirked to himself and then vanished before anyone could see him. The next few days consisted of Damon running around making plans while Stefan tried to figure out just what the hell his brother was up to this time. It was Saturday morning when Stefan finally figured out what was going on though it wasn't that hard to figure out when there were people all over the place setting things up. The Winchesters were just as bewildered as Stefan was, but the younger Salvatore managed to corner Damon first.

"What the hell is going on? I expected you to kidnap the bride not plan her damn wedding." Stefan said looking at his brother suspiciously.

Damon shook his head and smiled, "Oh I'm sure you're not the only one. She is having his baby, Stefan. He's given her the one thing that I can't. As her best friend, I figured, what the hell, I might as well try to be supportive. So that is what I am doing, Stefan. My gift to her is her dream wedding. The wedding that Ruby has always dreamed of having. Now that is one thing he can't give her."

"Okay who are you and what have you done with Damon?" Stefan asked still eying his brother suspiciously.

The older vampire's laughter echoed throughout the house as he walked away from Stefan. He was just grateful that Dean was still willing to go through with this after finding out about his and Ruby's indiscretion. The bride to be was in Damon's room along with Caroline, Elena, and Jenna who were already in their bridesmaid gowns. Jenna was working on Ruby's blonde locks while Caroline worked on her make up and Elena worked on her nails. It didn't take long to get her all done up for the wedding and once her dress was on, Jenna zipped the zipper up and Ruby turned toward the full length mirror only to gasp in shock. It was a modified version of her dream dress and it fit her perfectly. It was a spaghetti strapped ivory ankle length gown with a light dusting of sparkles on the corseted bodice. It flared out at her hips and with her hair in loose waves as it was, Ruby looked almost exactly like she would of looked had she married Damon before either of them had changed. As with tradition, her something blue was a garter courtesy of Caroline, her something new was earrings from Jenna, and her something borrowed was a bracelet from Elena. To Ruby's surprise, Elena handed her a black velvet box along with a folded note. She unfolded it and smiled when she recognized Stefan's handwriting. _**How appropriate that I be the one to give you something old. This belonged to mother and I can't imagine giving it to anyone else. Don't worry, Elena understands. - Stefan. **_Ruby smiled brightly and opened the box only to see a beautiful silver necklace nestled inside. She teared up and mentally cursed her pregnancy hormones.

A knock at the door alerted the girls that it was time to take their places and they headed downstairs. Ruby put the necklace on and spotted Damon in the mirror looking absolutely gorgeous in a tux. She turned around and smiled softly at him. Damon froze at the sight of her and if he had a beating heart, it probably would of been beating rapidly at the moment. It stung knowing that was how she would of looked on their wedding day, but he pushed those thoughts aside as he approached her. He kissed her softly on the lips careful not to mess up her make up and smiled.

Damon gazed down at her and brushed his thumb against her cheek lightly, "Beautiful as always. Now I believe there is a groom waiting for you at the altar."

"Thank you. Wait, you're giving me away? Is this a joke or something?" She asked as she linked her arm with his arm and raised her eyebrow at him.

He chuckled as he whisked her downstairs carefully and then stopped just before they got outside, "No joke. If you would rather Stefan give you away, I can go switch with him if you like."

"No no, it's fine, Damon." Ruby assured him and smiled as he handed her a bouquet of flowers.

Damon stepped outside with her and smiled to himself as he heard her soft gasp. It looked exactly how she had always imagined it would look like. The garden was redone to look just like it did back in the late eighteen hundreds except now it was the site of a wedding. Her wedding to Dean to be precise. She knew without saying a word that Damon had been behind this whole thing and it simply confused the hell out of her. In the case of worst possible timing, Ruby whispered something to Damon before rushing back into the house. He simply chuckled and assured everyone that she would be right back. She somehow managed to use the ladies room without ruining her dress thankfully and then washed her hands. As she dried them, a somewhat familiar voice began to chant and the pregnant blonde felt herself growing weak. Her legs gave out as everything surrounding her went black and her head smashed against the edge of the sink as she collapsed onto the floor. It didn't take long for Damon to realize something was wrong and he shared a look with Stefan before vanishing into the house. Stefan informed the Winchesters of the situation and the three of them took off after Damon into the house. The elder Salvatore brother had reached the bathroom first and horrified at what he saw. There was blood on the edge of the sink and a pool of blood on the floor. He stepped inside and knew just by the scent that the blood belonged to Ruby.

"Oh God! Damon.." Stefan trailed off knowing without his brother saying a word that the blood belonged to Ruby.

Dean quickly realized what was going on and pushed his way into the bathroom grabbing Damon by the lapels of his suit jacket tightly, "You just couldn't handle the fact that she chose me over you, could you, Damon? Where the hell is she?"

Damon, already angered by the sight of Ruby's spilled blood, went into full on vampire mode and slammed Dean back first against one of the bathroom walls, "First of all, I would never ever hurt Ruby, you jackass. I love her. Second of all, I have no idea where she is, but I can guarantee you that I will find her."

"Guys, please, this isn't helping anyone right now. We need to focus on finding Ruby." Sam spoke up as he and Stefan separated their older brothers.

It was the gravelly voiced angel that spoke up catching the attention of both sets of brothers at once, "Damon is right. He did not harm Ruby nor did he take her."

"Then who did?" All four men questioned simultaneously as Damon's face returned to its usual handsome form.

Her body laid limply in the trunk of a car headed across town from the Salvatore Boarding House. Blood stained her forehead, a little bit of her hair, and some of her dress a deep crimson shade. She was still out cold when the car stopped and she was pulled out of the trunk. Her body was brought inside and laid limply on a table in the center of a room. Her wrists and ankles were tied down before a short incantation was spoken which only awakened the pregnant blonde. A gag was placed over her mouth to prevent her from screaming and from reciting any spells.

Bonnie smirked as she picked up a book and began to flip through it, "Sorry Ruby. You know, I truly hate to do this. I mean, it is bad enough that we have vampires running loose around here, but the last thing that we need is a demon child on the loose as well."

The brunette witch stopped once she reached the page that she was looking for and began to recite again. The pregnant blonde's bright blue eyes widened as she realized what Bonnie was doing. It was a protection spell that was commonly used to protect homes from evil, but Bonnie was modifying it to keep out the very same four men that were currently searching for Ruby. If looks could kill though, Bonnie would be dead on the spot from the look she was currently receiving from the pregnant blonde.


	15. Chapter 15

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Fifteen:

Ruby struggled against the ropes that had her tied down, but it was no use. The ropes were tied too tightly. Bonnie set down the book that was in her hands and began her preparations to perform the spell that would ultimately rid Ruby of the baby. Back at the boarding house, the four men along with Elena and Castiel met up in the study after not being able to locate Ruby anywhere in Mystic Falls. Dean, Sam, and Elena remembered Ruby's trick in locating where Katherine had held the Salvatores though they were unsure if it would actually work this time around. Damon had been willing to try it though and did the honors with help from Elena. After Damon said out, the brunette teen was shocked to see that the only part of the map untouched was the spot where her best friend Bonnie's home was located. The Winchesters took off in the Impala while Castiel vanished and the Salvatores appeared outside of Bonnie's door with Elena in tow. Castiel appeared to the three of them a moment later with his trench coat billowing in the air as Dean parked the Impala.

Castiel looked around and then spoke up once the Winchesters joined them on the front porch, "Ruby is in the basement."

With that said, Castiel vanished again and Dean kicked the door open. The Winchesters along with Elena went inside only for the brunette to stop when Stefan cleared his throat. Dean laughed at Damon's predicament and looked around for the basement door. Damon growled in response only to be relieved when Elena invited them in. Sam found the basement door and grasped the doorknob only to be knocked back. The same thing happened to the other three men and Stefan refused to let Elena even try. In the basement, Bonnie could hear the movement upstairs and shook her head. Ruby tried to scream, but to no avail thanks to the gag in her mouth.

Bonnie smirked and picked up another book, "It is no use, Ruby. The spell is keeping them out, remember? Now to get this over with and you can be on your way."

She looked down at the book flipping through it to get to the right page. With her eyes off of Ruby for the moment, Bonnie failed to notice that the gag was removing itself from Ruby's mouth. The blonde took a deep breath once the gag was fully removed and then shouted out the spell that broke the protective seal around the basement. Bonnie was shocked and gagged her again. Having heard Ruby's shout, Damon got to the door first yanking it open and was by Ruby's side in the blink of an eye removing the gag. Elena made it down there next with assistance from Stefan and held Bonnie back as Damon untied Ruby. Stefan snatched the book from Bonnie shutting it amid Bonnie's protests.

Her eyes widened and she shook her head, "No, what the hell are you doing? Don't you understand? If we let her go through with this pregnancy, a demon child will be brought into this world. It'll destroy Mystic Falls and everyone that we care about."

"That is where you are wrong, Bonnie. This baby is half Winchester. That means that this baby has a good heart. Look, I may be a bitch, but I wouldn't raise my child to destroy everything." Ruby glared at Bonnie as Damon scooped the blonde up into his arms carefully.

Castiel appeared placing his hand over Ruby's stomach for a moment before looking over at Bonnie, "This unborn child isn't evil. He or She isn't even demonic. This baby is the product of pure creation. Bonnie, your fears are understandable, but Ruby is simply carrying a purely human child."

"That's great, but how is that even possible?" Elena asked curiously yet relieved that Bonnie's fears had been proven wrong.

Damon couldn't resist and as the angel healed Ruby's head wound, the vampire smirked at his brother's girlfriend, "Well Elena, when two people have sex.."

He trailed off as Ruby smacked him upside the head playfully. Elena rolled her eyes and scoffed at him. Once Ruby was healed, it took all the strength that Damon had in him to keep her from tackling Bonnie and ripping the younger girl's head off. He used his vampiric speed to whisk the blonde back over to the boarding house much to the not so subtle annoyance of Dean. The pregnant blonde was still struggling in Damon's arms when she realized they were in the parlor of the boarding house.

"What the hell, Damon? She tried to kill my baby! I have every right to kick her ass until she can't breathe." The blonde fumed as the vampire finally set her down on her feet.

Damon grabbed her upper arms gently forcing her look at him, "You're right. If you kicked her ass the way I know you would, though, you'd only be putting yourself and the baby at risk, Ruby. You have to calm down."

"Fine, I will calm down, but I reserve the right to be pissed at Bonnie." She huffed annoyed that she was being treated like a porcelain doll though she knew that she didn't want to risk hurting the baby.

The familiar roar of the Impala's engine could be heard as the Winchesters pulled up outside of the boarding house. Sam had managed to convince Dean to let Stefan and Elena deal with Bonnie. Back at Bonnie's, the brunette witch had finally calmed down and felt horrified by her actions. The thought that she almost killed an innocent unborn child chilled her to the bone. She knew that Castiel was really an angel and she knew deep down that he wouldn't lie about the kid not being evil. When Stefan was finally convinced that Bonnie would be okay and that Elena would be safe with her until Caroline showed up, he kissed Elena and then left for the boarding house hoping that it wasn't completely wrecked by now. Unfortunately when he got there it was all too obvious that Damon and Dean were verbally at each other's throats yet again.

Dean glared at the older Salvatore vampire unafraid of him as he had killed vampires before and wasn't scared to do so again, "She is my fiancée and she is carrying my baby. Ruby is coming with us, Damon. It isn't your decision."

"You know what? It isn't your decision either, Dean. I'm pregnant. I'm not a damn porcelain doll. I can still make my own damn decisions. Just like when I decided to say yes to your marriage proposal and when I told Castiel to keep his mouth shut about Damon snacking on him." She snapped annoyed that she was being talked about as if she weren't standing right there and then her bright blue eyes widened when she realized what she had just said.

He grew even more upset and tackled Damon to the ground, "You bit Cas?"

"Guys, calm down, alright? Yes Dean, my brother probably did bite Castiel. He is Damon. He bites people that he is not supposed to bite like Caroline." Stefan remarked and then cringed when he noticed the look on Ruby's face.

It was a mixture of disappointment, hurt, and anger. She pushed Dean away from Damon and the vampire sat up only to be on the receiving end of a bitch slap courtesy of the pregnant blonde. He rubbed his face and watched as she stormed upstairs. Sam had been silent the entire time taking in everything they had said and the wheels began to turn in his mind. Before Dean or Damon could react, Sam had already gotten to the stairs and was making his way up them. There was something he had to know in order to make sense of everything and Ruby was the only one he dared to ask. He knocked on Damon's door and it flew open only for the pregnant blonde to soften at the sight of Sam's puppy dog eyes. She let him in shutting the door behind him and turned her back to him. He understood after a moment and unzipped her dress.

"Thanks and I'm okay. These freaking hormones are just driving me nuts." She admitted with a slight smile and disappeared into the bathroom.

"No problem and yeah I figured that. Listen, Ruby, I have to ask you something and please don't get mad at me for asking. When did you sleep with Damon?" Sam asked though he couldn't see her and glanced around.

"What? Sam, I'm not mad at you for asking. It was the same night that he bit Castiel. I argued with him after Cas left and...it was just angry sex, Sam. It was wrong of me to cheat on Dean. I know that. You don't have to lecture me." Ruby spoke softer than usual as she stepped out the bathroom in jeans and a black tank top.

"I'm not going to lecture you, Rubes. Wait, you're going with us after all?" He asked somewhat surprised as he watched her pack.

"No I'm not. Sorry Sam. I'm staying with my friend Jenna. Keep in touch though, alright? I'd hate to not hear from my favorite Winchester." She winked at him and smiled softly when he pulled her into a giant hug.

Ruby waited until the Winchesters left before asking Stefan to whisk her over to Jenna's house which was a familiar route to him as Jenna just happened to be Elena's aunt. He agreed after she assured him that she would be fine there and it wasn't long before she was settled at her newfound best friend's house. She noticed Jenna's frustrations with her nephew Jeremy and frowned. Ruby was aware of the accidental death of Elena and Jeremy's parents. She was also aware of the deaths of Jeremy's last two girlfriends Vicki and Anna though she wasn't sure if Vicki counted as a girlfriend. Ruby was also all too aware of Jeremy's recent failed attempt to become a vampire after his vampire girlfriend Anna was killed for good. She knew Anna from way back in the day so that news had upset her somewhat. She flashed Jenna a reassuring look before sitting down beside Jeremy on the couch relieved that it was out of earshot of Jenna who was in the kitchen.

"Hey Jeremy. Listen, can we talk for a minute?" She asked being unusually nice for once.

He looked at her and rolled his eyes, "Look, I know what you're going to say and you're wrong. You don't know what I'm going through. No one does."

"Okay first of all, that is where you are wrong. I know exactly what you are going through. I never had a dad, but I did have mom. A vampire drank all of her blood and just left her dead body there for me to find. I had to watch helplessly as my mother's dead body burned in a fire. I also know what it is like to lose the person you love, Jeremy. I lost mine twice." Ruby told him and wiped away a few stray tears mentally swearing at her pregnancy hormones.

Jeremy softened as he considered what she said and then nodded his head, "Alright, maybe you do understand. We can talk for a minute if you want."

"Good. Listen, I also know that you tried and failed to become a vampire. Just do me a favor and don't try that again. Not being human isn't as great as you think it might be. You change. You become dark, lonely, cynical, careless, sarcastic, and it is hard as hell to hold on to that piece of humanity that still lingers inside of you. Look, Jeremy, you're not the only one that lost your parents. Elena did too. She is moving on with her life just like your parents would of wanted both of you to do. Hell, I moved on with my life too and look at me. I'm going to be a mom." She said hoping that she was getting through to the younger boy.

He nodded his head again and smiled softly, "Thanks and you're right. There is this girl I've always had a crush on."

"Well there you go. You don't have to rush anything, you know. At least talking to her is a start. Oh and be nice to your aunt and Elena. They are just doing the best that they can, alright?" Ruby remarked and looked at him.

Jeremy glanced back at his aunt before smiling at Ruby, "I will, I promise. Oh hey Ruby, by the way, you're going to make a great mom."

Ruby didn't know what to say so she pulled him into a hug instead. He hugged her back and chuckled as she ruffled his brown hair gently. When she pulled away, Ruby smiled proudly as she watched Jeremy walk over to Jenna pulling her into a hug. His aunt looked at Ruby thankfully and smiled. The pregnant blonde returned the smile and headed upstairs. She showered before changing into her pajamas and crawled into the bed that was in the guest bedroom. She sighed contently as she relaxed against the pillows and smiled as Jeremy's words echoed through her mind. As she slept, Ruby was blissfully unaware that she wasn't alone in her bedroom. He watched her as she slept and gently brushed his fingers along the side of her soft beautiful face. He had heard her conversations with both Sam and Jeremy tonight. He knew Jeremy's statement would prove to be more than true. Ruby would most definitely be a great mom. He was gone by the time her bright blue eyes fluttered open the next morning. The scent of breakfast in the air made her smile for a moment before she paled and ran to the bathroom. Had she looked over at the window she would of noticed the black bird perched upon the windowsill as if guarding over her.


	16. Chapter 16

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers.

Chapter Sixteen:

When she finally felt well enough to attempt eating something, Ruby went downstairs joining Jeremy, Elena, and Jenna for breakfast. The older woman sensed that Ruby was hit with morning sickness as the pregnant blonde looked paler than usual so she set a plate of toast down in front of her along with a glass of ginger ale. The news was on and a report of an animal attack caught the attention of all four of them. Elena and Ruby shared a look agreeing without words to visit the Salvatores after eating. It didn't take long for them to finish eating, get dressed, and head over to the boarding house. Though Elena knocked on the door, Ruby rolled her eyes and simply walked in not caring to wait for one of the brothers to answer the door. The pregnant blonde sprawled herself out on the couch getting comfortable while Elena greeted Stefan. It was barely a moment later when she felt her head being lifted and she glanced up only to meet Damon's piercing blue gaze. Of course it was then that she realized that her head was now resting on Damon's lap. She simply shrugged and waved at him before looking over at his brother.

"So according to the local news this morning, there was a report of a body found just outside Mystic Falls. Throat was ripped out, but there wasn't a huge bloody mess like there should of been. The cops are blaming the lack of blood on the rain washing it away though. Elena and I on the other hand know better. It was a vampire, wasn't it?" Ruby asked turning her head to fix a pointed glare at Damon.

Damon looked down at her and chuckled as he pushed her blonde locks away from her face, "It wasn't me, I swear. I've surprisingly been more careful lately."

"Well if it wasn't either of you then who was it?" Elena questioned with concern evident in her brown eyes.

Before either of the Salvatore brothers could reply, the all too familiar roar of a car engine could be heard. Ruby smiled knowing it belonged to the Impala though she also noticed the way Damon tensed. She made no effort to move though as Stefan let the Winchesters in and shut her eyes as Damon stroked her golden hair softly. Luckily for her, Stefan explained Ruby's situation along with the fact that they were all aware of the attack before he led the brothers into the living room.

"We checked out the scene of the attack on our way back into Mystic Falls. Didn't find much so we hit the coroner's office. Get this. The autopsy isn't done yet, but the preliminary report states that there was no blood found in the body. An animal attack would leave at least some blood in the body." Sam informed them as he sat down in a nearby chair.

Damon glanced down at Ruby before looking over at Stefan, "Looks like there's a vampire on the loose after all. Let's have a party."

Ruby rubbed her stomach lightly and rolled her eyes at Damon's sarcasm. Across town, people from all over Mystic Falls were arriving at the Lockwood Mansion to pay their respects to the family of the late Mayor Lockwood. His son Tyler was sick of hearing all of the condolences and everyone saying that his father was a good man. It wasn't true. He knew the truth. His father was an abusive jerk that often butted heads with him. Tyler needed some fresh air so he maneuvered through the mourners and found his way out the front door. He took a deep breath of the fresh air and glanced around only to freeze when he saw her. She was a vision in black. From the strappy heels on her feet to the black sunglasses covering her eyes. She was wearing a black dress that stopped an inch or two above the knee yet seemed to hug her every curve perfectly. A black leather jacket was on over that and the sleeves were pushed up to her elbows exposing her creamy porcelain skin. Her lips, however, were a glossy shade of blood red.

Tyler snapped out of his daze just as she approached him, "Uh, hi. I don't believe we've met. I'm Tyler Lockwood."

"You're right. We haven't and it is a pleasure to meet you. I'm Lily." The brunette smiled flicking her loose brown locks over her leather clad shoulder and pushing her sunglasses to the top of her head.

He smiled admiring her up close and was almost taken aback by how shockingly blue her eyes were, "Well it is a pleasure to meet you too, Lily. I wasn't aware that my father knew someone as beautiful as you."

"That's because he didn't. I'm only here on behalf of my family to pay respects. This is such a drag. You know half these people are only here to be polite since he was the mayor and all. It's ridiculous." Lily scoffed and then smiled at him.

Tyler smirked as he felt the same way that she did, "My sentiments exactly. Come on, I'll take you to my mom and then you can go if you'd like. Up to you."

She nodded her head following him up to the front door of the Lockwood Mansion. Tyler walked inside expecting her to just follow him in, but looking over his shoulder he saw that she was standing just outside the doorway. He walked back to her with a confused expression upon his face. She noticed it and smirked softly.

"You didn't invite me in, Lockwood." Lily remarked with a slight giggle as he checked her out again.

He smirked and nodded his head, "Come on in then, Lily with no last name."

"Thanks." She winked at him and stepped inside brushing past him teasingly before making her way to pay her respects to his mother Carol.

Back at the boarding house, Ruby had fallen asleep with her head on Damon's lap. Dean was keeping a close eye on them and Elena just shook her head as she draped a blanket over the pregnant blonde. Stefan could tell that something was on Sam's mind and wasn't surprised when Sam looked at him gesturing to the study. He nodded his head and walked into the study with the tall Winchester brother.

"Alright, look, Stefan, I've been thinking a lot lately and something just doesn't add up about Ruby's pregnancy." Sam said looking at the younger Salvatore brother.

"What? You don't think she's faking it, do you?" He questioned raising his eyebrow at Sam.

"No, God no. Ruby would never do that. I'm just saying that I'm not sure that I believe that my brother is that kid's father. So I was just kind of wondering if you could tell me how different blood affects vampires." He remarked noticing the surprised look upon the younger Salvatore's face.

"Well, blood is blood. A vampire can sustain itself just fine off of animal blood, but won't be as strong as a vampire that regularly feeds off of human blood. Demon blood, however, can make a vampire such as my brother more aggressive, more passionate, more reckless. Although, the only demon blood I've ever seen Damon drink was Ruby's so it is possible that it is not the blood's effect on him, but Ruby's effect instead." Stefan informed him and glanced over at his brother for a moment.

"What about angel blood? How might that effect a vampire?" Sam asked curiously to see if maybe his theory was correct.

"I wouldn't know. Vampires and angels don't exactly cross paths often." He shrugged his shoulders wondering what Sam was getting at only to turn when the angel in question appeared.

Castiel looked at them both before looking at Sam, "Angel blood is not just blood, Sam. It also has the angel's grace within. Damon not only got a taste of my blood, he got a taste of my grace as well."

"The grace, that's it! Oh, uh, sorry Stefan. There was this girl Anna Milton. Both the angels and the demons wanted her. Dean and I tried to keep her safe. Turns out she was a fallen angel. She ripped her grace out and fell to earth. Literally. When her grace landed though instead of pure destruction, it was pure creation. A centuries old tree appeared in the very spot that her grace is in. Now back at Bonnie's, Cas said that Ruby's baby is the product of pure creation. How much do you want to bet that child is a Salvatore?" Sam asked unaware that Damon could hear every word that he just said.

Of course Damon made no outward reaction to give anyone the impression that he had heard that conversation. Ruby woke up moments later when he tried to move her and it wasn't long before she headed back to Jenna's with Elena. She showered and changed into a more comfortable outfit. As she stepped out of the bathroom, Ruby nearly jumped ten feet in the air when she saw Damon just sitting on the edge of her bed. She swatted his arm playfully as she walked past him and then turned to look at him.

"Are you drunk?" The blonde raised her eyebrow at him noticing there was something off with the vampire.

Damon made a gesture with his fingers and squinted his eyes at her, "Just a little bit."

"What's wrong?" She asked as concern shone in her bright blue eyes.

He grasped her left hand and gestured to her engagement ring, "That's wrong, Ruby. I love you more than he ever could. Hell, you wanted to marry me first."

"Damon, I love Dean. I'm sorry, but it is always going to be Dean." Ruby admitted softly as she looked into his pale cerulean eyes.

The older Salvatore brother shook his head letting go of her hand and stood up facing her, "Stop lying, Ruby. You are lying to me, to everyone around us, to yourself and I'm going to prove it."

Before she could say another word, he had grasped her face within his hands pulling her into a passionate kiss. She resisted him at first trying to push him away until she finally gave in returning the kiss. His hands slid down to rest on the slight swell of her stomach and that is when she finally had the strength to push him away. They looked at each other and she glared at him.

"Damon, you can't just come in here and kiss me like that. I'm engaged to Dean. I love Dean. I'm having his baby. I finally made a choice. If you can't handle that than I am sorry." She informed him unaware that the next thing he said would change her life forever.

His blue stare pierced right through her as his lips twisted into a smirk, "It's not his baby, Ruby. You can thank your angel friend for that the next time that you see him."

"I don't know what you are trying to pull, Damon, but joking about the paternity of my child is not funny." Ruby glared at him even more.

Damon frowned and then narrowed his eyes at her, "I'm not joking about our child, Ruby. That's right. Our child. Conceived the night I had a taste of angel blood."

"Everything alright in here?" Sam asked as he stepped into the guest bedroom with concern in his puppy dog like eyes.

He was in front of Sam in the blink of an eye and pinned him to the wall, "Always the weak brother, huh Sammy? How would you like to finally be the strong one? More powerful than you and Dean could ever imagine."

"Damon, No! Get away from him! Please!" Ruby cried out in horror at the sight of the crimson liquid oozing out of the vampire's pale wrist.

She knew that her words wouldn't be able to stop him so she did the only thing that she could think of. Ruby squeezed herself between him and Sam pulling the raven haired vampire into a steamy kiss. It caught Damon off guard for a moment and then in a blink of an eye, they were both away from Sam. Damon broke the kiss first and looked at her. She looked back at him with tears glistening in her bright blue eyes. He instantly felt guilty and the expression on his face reflected that.

"You are so lucky I am pregnant right now or I would kick your ass for trying to pull a stunt like that." She said giving him a harsh glare as she knew he was hurt and that he had a habit of doing stupid things when he was this upset.

Damon nodded his head hearing Dean walking up the stairs. Without a word, the dark haired vampire vanished from the room in the blink of an eye. Ruby let out a breath she hadn't realized that she was holding and walked over to Sam making sure that he was okay. His large hands rested on her stomach for a moment as he gave her a look and she knew just by that look that Damon had been telling the truth about the baby. Ruby took a few steps back and sat down on her bed letting her mind process everything that had just happened. Dean walked in just then and sat down next to Ruby as Sam filled him in on what happened. Even though Dean wanted to rip Damon to shreds for nearly turning Sam into a vampire, He knew that killing Damon would only hurt Ruby and that he was to blame for Damon being upset in the first place.

_Dean watched as Elena and Ruby pulled away from the boarding house in Elena's car before he walked back into the boarding house, "Damon, we need to talk."_

_The vampire poured himself a drink and smirked slightly, "Oh, do we? Finally come to realize that I'm the only one for Ruby?"_

_He rolled his eyes and scoffed slightly, "No. I've finally come to realize that you are obsessed with my fiancée. Look, man, I get that you love her. So do I, but she is having my baby. I know I can't keep you and Ruby from being friends. I'm just warning you that if you go anywhere near my kid, I will cut your damn head off."_

_Damon sipped his drink and chuckled sarcastically, "Your kid? Do you really think that I would harm Ruby's kid? Are you out of your damn mind?"_

_Dean shook his head and smirked at the vampire, "No, I'm not. I know what you are, Damon. I've killed plenty of your kind before and I'm sure I'll kill plenty more. You are a vampire. You are a cold blooded monster, Damon. She doesn't love you. If anything, she loves the memory of the Damon you used to be before Katherine turned you."_

_He downed the contents of his glass and filled it again tossing a smirk at Dean, "And? Ruby's a demon, Dean. You've killed plenty of those too, I'm sure. Oh, you don't know, do you? I'm the father to be. Not you. Apparently angel blood does wonders for the vampire libido."_

_The elder Winchester froze and then glared at Damon, "I wouldn't get too excited about that, if I were you. Do you really think that Ruby would raise her child with a cold blooded monster? Don't you get it, Damon? Deep down inside, Ruby wants that kid to be a Winchester. She wants me to be the father because she loves me and she wants Sam to be the kid's uncle because he's the little brother that she never had. She'll never love you the way she loves me."_

_Before Damon could respond, Dean left the boarding house with Sam leaving Stefan the impossible task of calming his older brother down._

Lily was surprised to find herself enjoying the time she was spending with Tyler Lockwood despite the sad circumstances that had brought them together in the first place. He was going through a rollercoaster of emotions as a result of his father's untimely death though anger seemed to be the most apparent. What was surprising to him was how calm and at peace he felt just by Lily's presence. He had initially sensed that there was something different about her, but he didn't know what exactly. Their lips were a breath apart when she suddenly pulled back and stood up.

"I'm sorry. I should go. I'm late for a very important meeting." Lily said and leaned down brushing her lips against his cheek gently.

Tyler smiled softly and went to turn his head to catch her lips only to frown when she pulled back, "What? Afraid to really kiss me?"

"Never. The wait is half the fun, you know." She winked at him on her way out of the study waiting until she was outside to vanish in the blink of an eye.


	17. Chapter 17

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers. Lyrics are from the song "Learn to be Lonely" from the Phantom of the Opera soundtrack.

Chapter Seventeen:

Mason Lockwood had returned to Mystic Falls for his older brother's funeral and had been keeping an eye on his late brother's only child Tyler since then. He was fully aware that the teen had begun to go through the changes in becoming a werewolf like Lockwoods before him. With his brother gone, the responsibility of showing Tyler the ropes so to speak fell squarely on Mason's shoulders. Of course his werewolf senses went on alert the moment Tyler had entered the mansion with the brunette that he knew, via his sister in law, went by the name Lily. Having been a full on werewolf longer than Tyler who was just starting to go through the changes meant that Mason's senses were more fine tuned in sensing things that were amiss. He was brought out of his thoughts at the sound of his nephew's outburst and pulled his nephew into the study where he knew they wouldn't be interrupted.

"Calm down, I know you are upset, but flipping out at your mother isn't helping matters." Mason spoke calmly yet firmly at his teenage nephew as he sat down with him on the couch.

Tyler rolled his eyes and then looked at his uncle, "I'm trying. I'm just frustrated. I know Dad didn't die of a heart attack and she knows that too."

"I know he didn't. Alright, it's time that you knew the truth, Tyler. The Lockwood family has a deep dark secret. Dating back to our ancestors, the Lockwoods have been werewolves. It all started with one Lockwood being bitten by a werewolf and then it all just became genetic from there." He admitted not surprised by the look of disbelief on his nephew's face.

He looked at his uncle and laughed, "That is crazy. Werewolves only exist in movies, books, and TV shows."

"I'm telling the truth, Tyler. Ever wonder why you keep having moments where your eyes change to glowing yellowish orange hue? Or why you've grown more temperamental? Or why your senses are becoming more sharper? It's the werewolf changes, Tyler. You'll be a full one by the next full moon." Mason informed his nephew bluntly knowing sugarcoating it just wouldn't cut it.

Tyler raised his eyebrow and sighed, "Alright, say I believe you, does that mean that Dad died from a silver bullet or something?"

"No no, your father wasn't shot as far as I know. Look, now that you know about the family secret, there is something else that you should know. There are other things out there that exist. Witches for one and Vampires for another. Vampires can't get into the house unless they are invited in. Don't ask, I can't explain. It just is what it is." He explained to his nephew who appeared to be perplexed.

His thoughts flashed to Lily for a moment before rethinking that notion and then he looked at his uncle, "So basically I'm going to turn into a hairy freak when there is a full moon. Great. Thanks for letting me know."

As Tyler walked out of the room, Mason shook his head knowing it would take some time for his nephew to wrap his head around everything he had just learned. Over at the Gilbert home, Ruby was amused at the sight of Sam and Jeremy playing a video game in the living room. It was nice seeing Sam acting..well..normal. She rested her hand on her baby bump and sighed softly as she made her way upstairs to the guest room that she was currently staying in. The pregnant blonde shut the door behind her and crawled into bed snuggling into Dean's side.

The elder Winchester brother sighed and kissed her head softly, "So you are carrying a Salvatore, huh?"

"Dean..." Ruby trailed off unsure of what exactly she could possibly say in response to that.

He shook his head and draped his arm around her, "Why him, Ruby? I just don't get how you could of loved such a cold blooded monster."

"He wasn't always a cold blooded monster, Dean, and don't call him that. To be honest, I was arranged to marry Stefan, but my mother broke off the arrangement because she couldn't stand to see her daughter marry a man that she didn't romantically love. I mean, Stefan and I had become good friends. I just didn't love him like that. With Damon, It was almost like a tornado meeting a volcano, even back then. He was a gentler Damon. The Damon that you hate now is the Damon that Katherine put through the wringer. Most of his bad qualities he got from her." She explained and bit her lip softly.

Dean stayed quiet for a moment and then frowned, "So why are you still friends with him if he isn't the same Damon?"

"Because he still is the same Damon. To me, at least. After Katherine got me turned into a demon, I fought and clawed my way back out of hell. I returned here to Mystic Falls just in time for that raid they did that ended with a bunch of vampires being killed in a fire at the old church. Katherine was believed to be one of them. Damon and Stefan had actually tried to free the bitch. You know what they got for their efforts? Shot by their own father. I was the last thing that they saw before they died. When they came to, I freaked the hell out at first before realizing that Katherine had turned them. Stefan was the first to complete his transition, but Damon wanted to just die. I showed him my onyx demon eyes and he wasn't freaked out by it at all. He stared at me as if I were the most beautiful woman he had ever seen. I was selfish, Dean. I didn't want him to die so I cut myself and made him drink. So when Stefan brought around a girl to help his brother finish the transition, Damon just couldn't resist tasting her blood." Ruby admitted as she rubbed her stomach softly.

He held her close and sighed, "You weren't selfish. You loved him, Ruby, and you just didn't want to lose him."

"Look, enough about Damon right now. What are we going to do about us?" She asked turning her head to look at him.

Dean stared at her for a moment before smiling softly, "I'm going to make you my wife. I love you and that is not going to change because you are having his kid."

Ruby simply murmured in agreement and snuggled into his side quietly. As much as she wanted to be his wife, part of her felt guilty that she was laying in bed with him while she was carrying Damon's child. A haunting thought struck her just then and she slid out of the bed muttering something about needing a drink. The pregnant blonde went downstairs as if she were heading to the kitchen to get something to drink, but snuck out front instead making her way to the Salvatore boarding house. Meanwhile, at the boarding house, Damon and Stefan were in the library discussing the latest so called animal attacks that seemed to be getting closer to Mystic Falls. Her glossy crimson colored lips twisted into a smirk as she walked through the house hearing their voices as she approached the library. She stopped just as she reached the open doorway of the library and smirked more as they both looked at her having sensed her presence.

"Hello brothers." Lily smirked as she greeted her older brothers though one was obviously a bit more shocked to see her than the other.

Damon smirked slightly giving his little sister a knowing look before rolling his eyes, "Lily. Well, at least now we know the animal behind the attacks."

"Lily? Oh my god, but how?" Stefan asked completely shocked to see the little sister that he had believed perished long ago.

He looked at them and nodded his head, "Oh right, I knew there was something I was forgetting to tell you, Stefan."

"Stefan! It's so great to see you, big brother. I missed you so much." She squealed slightly as her big brother pulled her into a hug swinging her around lightly.

Damon scoffed and then grinned softly when he got his turn to hug his sister, "Nice to see you too, little sis."

"You knew all this time and you didn't think to tell me, Damon?" He glared at Damon throwing the older man across the room into a wall.

"Stefan, stop it. He saved my life. I had just given birth to twins. A boy and a girl. There was complications though and there was so much blood. Damon found me and gave me some of his blood. It was too late though. I died shortly after with his blood in my system. He compelled the doctor to not pronounce me dead and I came to. Because of Damon, I got to raise my children, Stefan, and for that I will always be eternally grateful to him. Of course faking your age was so much harder back then compared to now. I had to fake my death once they were teens. I watched them from afar until I just couldn't take it any more and ran." She informed her older brother and picked up the letter opener twirling it with her hand.

He stood up brushing himself off and smirked at Stefan, "Yeah Stefan. I saved her life."

"Yes you did and you also took the life of my descendant Zach. Dick move, Damon." Lily remarked right before stabbing her oldest brother right in the stomach.

She was smart enough to move across the room in the blink of an eye, but unfortunately for her it was just as Ruby was walking in. The pregnant blonde had seen what happened and her eyes turned a purely onyx hue. She lunged at the brunette without thinking only for Lily to catch her off guard. The brunette vampire stood behind Ruby gripping her tightly and brushed the blonde locks away from the creamy white skin of her throat.

"Demonic and pregnant? Do you know, bitch, how deliciously rare your blood is right now? Bet it would of been a cute kid. Too bad you'll never know." The whites of Lily's eyes turned red as the veins around her eyes became more prominent and she tilted Ruby's head as her fangs extended preparing to have a taste of the blonde.

Damon had by then pulled the letter opener out of his stomach and was almost healed by the time he got to them grabbing Lily by the throat slamming her against a wall while Stefan caught Ruby sitting her down, "Sister or not, I will rip your damn head off if you ever touch her or my kid like that again."

"Your kid? I thought vampires couldn't procreate." She choked out as her vampiric appearance vanished and her blue eyes softened as she looked into her oldest brother's identical blue eyes.

He smirked slightly and finally let her go, "Yeah well apparently they can if they drink some angel blood beforehand or so I have been told."

"Okay why don't we leave the parents to be alone and go catch up?" Stefan suggested grabbing his little sister's arm and whisking her out of the library.

Ruby's eyes had returned to their normal bright blue shade by then and she was in awe of the fact that Damon hadn't vamped out when he had slammed Lily up against the wall. Her emotions got the best of her and she stood up walking over to him. He turned around looking at her curiously only to be surprised when she wrapped her arms around his now healed waist and hugged him tightly. Damon returned the hug and swallowed hard when she gazed up at him.

"I just came by because I had to ask you something. Did you know that consuming the angel blood would affect you in the way that you did which caused me to end up pregnant?" Ruby asked staring up into his pale cerulean eyes.

Damon gazed down at her and sighed, "It made me feel like god damn Tinkerbell, Ruby. If I had known, I wouldn't of drank the damn angel blood. Speaking of, you would look pretty damn hot in a Tinkerbell get up."

"Not with this baby bump, but thanks anyway." She found herself giggling softly only to bite her lip when she glanced down seeing Damon place his palm flat on her stomach shakily.

Ruby placed her hand on top of his hand and smiled softly. They remained like that for a few minutes before she kissed his cheek and left. Stefan returned just then with Lily and the brunette insisted that both of the boys join her at the high school carnival. She split from them a few moments after they arrived when she spotted Tyler. She kissed his cheek and watched as he arm wrestled with various guys. A few feet away, Damon and Stefan were watching as well. Damon was convinced that something was up with the Lockwoods and he was also none too pleased that his little sister was a bit too close to Tyler. Stefan was also concerned for their sister, but he wasn't quite sure if he believed Damon's theory that something was amiss with the Lockwood family. As if on cue, Mason Lockwood was the next to challenge his nephew in arm wrestling and won.

Damon spoke up just then to the surprise of everyone and Lily cursed her luck, "My brother Stefan would love to challenge you next."

"I would?" He questioned and looked at Damon.

Tyler smirked looking over at the Salvatore brothers only for the smirk to fade slightly when he realized that Damon had Lily's eyes, "Come on, Stef."

A smug grin crossed Damon's face as he nudged his younger brother forward, "Yeah, come on, Stef."

Lily elbowed Tyler in the side lightly and she walked away annoyed at her brothers. Tyler watched his uncle beat Stefan and then went after the brunette. He found her in line for the ferris wheel and grasped her hand interlacing his fingers with hers. She bit her lip before smiling softly at him. They got on the ride and once they were at the top, he turned to her speaking up before she could.

Tyler looked into her eyes and brushed a dark strand of hair away from her face, "Did you know that Damon Salvatore has eyes identical of yours?"

"Yeah I did. Listen, Tyler, I haven't exactly been honest with you. My name is Lily. Lily Salvatore. Damon and Stefan are my brothers." She admitted and looked at him.

He stared at her for a moment and then nodded his head, "Well now him having your eyes makes sense. I didn't know they had a sister."

"My brothers don't like to brag much. Now, we are at the top of the ferris wheel. Are you going to keep talking about my brothers or are you going to kiss me?" Lily asked with a playful glint in her eyes only to smile as he leaned in pressing his lips to hers in a searing kiss.

Damon ignored Stefan's protests and approached a carnival worker named Carter using his compulsion on the young guy, "You are going to pick a fight with Tyler Lockwood. You are not going to let up even if he hits you. You will not harm the brunette girl named Lily that is with him."

"That was completely uncalled for, Damon." Stefan said once Carter walked away from them.

He shrugged and folded his arms across his black button up shirt clad chest, "Maybe, but at least we'll know what we have to protect our sister from. Besides, you told me yourself that his uncle beat you even when you were using your full strength. You agree that something is not right. Just watch. When Tyler gets into a fight with Carter, his uncle Mason will show up."

By then, Tyler was off of the ferris wheel with Lily and they were walking through the parking lot to his car hand in hand. Her brothers hid behind some bushes watching as Carter walked by them knocking into Tyler's shoulder. Just as Damon predicted, the two started arguing with each other. Lily tried to intervene by compelling Carter only to realize that it wouldn't work because he was already compelled. Before she could even look for her brothers, Tyler and Carter began fighting right there in the parking lot. She stepped back fighting the urge to get involved only to gasp softly as Tyler's uncle came out of nowhere leaping off of a car kind of like a dog. Lily was in shock and was even in more shock when she along with Tyler saw Mason's eyes had turned into a glowing yellowish orange hue. Mason ended the fight and walked off with his nephew who grabbed Lily's hand. She went along with them and as she glanced over her shoulder, her eyes met Damon's identical blue eyes. Stefan helped Carter to his feet lying about what really happened and once Carter walked away, the younger Salvatore brother shared a look with Damon before the older Salvatore brother took off.

"L..Look Tyler, I should really just go. I'm sure my brothers are probably wondering just where the hell I am. Aside from the whole fight, I had a great time tonight." Lily smiled softly at him as they stood in the foyer of the Lockwood Mansion and then walked out as the way Mason was glaring at her made her feel uneasy.

Tyler ignored his uncle's protests and ran out the front door after the brunette, "Lily, wait!"

"What?" She asked as she turned around only to get pulled into a kiss by the handsome jock.

He pulled back after a few moments and smiled at her as they tried to catch their breaths, "I had a great time too. We should do it again sometime."

"I'd love to. Call me or..you know..text." Lily gave him her number and winked as she walked away.

When she was out of sight, Lily felt herself being grabbed and nearly screamed only for a hand to cover her mouth. Her face vamped out and she bit the hand that was over her mouth before tackling her attacker. Her attacker shoved her off causing her to smack into a tree. She stood up ensuring that she didn't have any wood sticking into her before facing her attacker only to see that her so called attacker was just her brother Damon.

"What the hell is your problem, Damon? I could of killed you!" Lily asked breathing heavily as her face returned to its normal state.

Damon shook his hand out as it healed and looked at her, "Relax. I was just making sure that you were okay. You didn't realize it was me until just now which means your senses are off. Have you been feeding properly?"

"I'm fine. I was about to go eat when you attacked me, jackass." She shoved him and kept walking only to be whisked away by him back to the boarding house.

He sat her down in the library and ran out of the room only to return in the blink of an eye, "Here. Drink this. You'll feel better."

"Thanks." Lily took the glass filled with the warm crimson liquid and sipped on it hungrily.

Damon nodded his head at her and took a sip from his own glass though it was filled with scotch instead, "You're welcome. That was from my own personal stash. Try not to get used to it."

"You sound like you are talking about drugs not blood, Damon." She laughed and licked her lips.

He rolled his eyes playfully and took another sip of his drink, "Don't get used to those either."

"Aww look at you! Already sounding like a dad. You're going to do great, Damon." Lily teased him and then smiled genuinely at her oldest brother.

Damon flashed her a brief smile before staring into the depths of the fire that was roaring in the fireplace. He was finally realizing that Stefan was right. He was going to be alone for the rest of his eternal life. Stefan had Elena. Ruby had Dean. Hell, even Lily seemed to have Tyler though Damon also knew that he and Stefan would have to talk to Lily in regards to the Lockwoods. When it all came down to it though, Damon Salvatore was just learning to be lonely all over again.

_Learn to be lonely_  
_Learn to find your way in darkness_  
_Who will be there for you_  
_Comfort and care for you_  
_Learn to be lonely_  
_Learn to be your one companion_


	18. Chapter 18

**Disclaimer: **I do not own anything you recognize here. TVD and SPN both belong to the CW. Anything recognizable belongs to the creators of the shows along with the writers. All I own is Lily.

Chapter Eighteen:

With Dean off hunting with Sam a few states over and Damon avoiding her, Ruby was on her own for a while dealing with her morning sickness or so she thought. A light knock at the door caught her attention as she relaxed somewhat comfortably on her bed and she told whoever it was to come in only to be pleasantly surprised when she saw that it was Stefan. He shut the door behind him and she gestured for him to come over to her which he did only to end up on the receiving end of a bear hug from Ruby. She hadn't seen him since Lily nearly killed her and she had missed him.

"So how are you feeling?" He asked as he sprawled out beside her on the bed with a look of obvious concerned etched across his handsome chiseled features.

"I'm okay. More than ready for this morning sickness to be over actually. How are you? Is Elena aware that you ditched her in her own house to hang out with the mother of Damon's unborn spawn?" Ruby asked flashing a teasing smile in his direction as she turned her body trying to make herself feel more comfortable.

"I'm fine and yes she is well aware. She actually went out shopping with Caroline. That should occupy her for a few hours at least. Spawn? I thought you were okay with the baby?" Stefan chuckled and then raised his eyebrow at the pregnant blonde beside him.

"I am. I love him or her. I'm just hormonal and really annoyed at your brother. Speaking of siblings, how are things with your little sister?" She looked at him and smiled softly.

"Who isn't annoyed at him? He'll come around. Just give him a little time. Actually, things are going pretty well with Lily. She's dating Tyler Lockwood of all people. Damon isn't too thrilled about that since it turns out the Lockwoods are werewolves." He informed her only to get his arm swatted at.

"When were you guys planning on telling me this? You do realize that Sam and Dean are hunters right? If Tyler goes terrorizing the town every full moon, they'll hunt him down and the last thing I want is Lily attacking them to avenge her boyfriend's death. Stefan, why are you laughing? It's not funny!" Ruby smacked his arm harder though she knew it probably didn't hurt him.

"Because we knew you'd freak out like this and stress isn't good for the two of you, Ruby. Tyler hasn't fully transitioned into a werewolf yet anyway. His uncle Mason has, though, but he takes the proper precautions every full moon to ensure that he doesn't hurt anyone." He assured her and chuckled softly.

"Whatever. Aunt to my unborn child or not, I will kick Lily's ass and drive a stake into her heart if one hair is harmed on either of the Winchester's heads." Her eyes flickered to their onyx hue briefly before returning to their normal bright blue state when she winced slightly.

"Ruby? Are you okay? Maybe I should get you to a doctor." Stefan said sitting up looking at her in concern as he didn't want anything to happen to her or her unborn child.

She stubbornly shook her head and Stefan opted to find Jenna instead. Luckily for Ruby, Jenna remembered a lot from when her late sister Miranda had been pregnant with Jeremy. She assured Stefan and the pregnant blonde that the same thing happened to Miranda when she got too worked up early in her pregnancy. They were both relieved and Stefan vowed to himself that he'd do what he could to ensure that Ruby stayed mostly calm throughout the rest of her pregnancy. As he escorted her over to the hospital just to ensure that everything was okay, His sister Lily was over at the Lockwood Mansion helping prep for the upcoming masquerade party. The way Tyler's Uncle Mason kept eying her gave her the creeps even though she knew he was only keeping an eye on her because he could sense that she was a vampire or at the very least he could sense that she was different. She ignored him the best that she could and was perfectly content spending the day with Tyler.

"Hey, how are we supposed to get anything done if you can't keep your hands off of me?" She asked giggling softly against his lips before pulling away.

Tyler chuckled as he stood behind her and pushed her dark locks off to the side as he dropped a kiss onto her neck gently, "Who said I wanted to help with the prep?"

"You did when you invited me over here in the first place." Lily laughed softly and glanced at him over her shoulder only to spot his mother off in the distance talking to Elena.

He followed her gaze and chuckled even more, "Mom's distracted. Good. Come on."

Lily simply laughed softly as Tyler grasped her hand gently tugging her out of his mother's sight and then walked with her to his car. He drove her away from the Lockwood mansion and away from the cautious eyes of his Uncle Mason. Damon, in the meantime, was over at the boarding house pouring himself a drink as he heard a car pull up. He lazily strolled toward the front door with drink in hand only to realize that it was Jenna Sommers. A very upset Jenna Sommers at that.

Damon swung the door open and leaned against it with a smile, "Jenna, lovely as usual."

The auburn beauty glared at him lightly and scoffed, "Cut the crap, Damon. I know that she's carrying your kid. You are such an ass, you know that? When Ruby needed you the most, It was Stefan that had to step up to the plate in your place."

Concern shone in his piercing blue eyes as he let Jenna in and shut the door behind him, "What are you talking about? Just because I haven't talked to her doesn't mean I'm not there, Jenna."

Jenna rolled her eyes and pulled a small white envelope out of her purse, "Here. She had some minor cramping so Stefan and I took her over to the hospital. Both mother and unborn child are fine. Just a bit too much stress. Anyway, Ruby wanted you to have that. She's home now resting."

Damon listened to every word she said as he took the envelope opening it only to pull out what appeared to be a sonogram photo, "Wow."

She couldn't help smiling softly though at the awestruck look on his face as he stared at the photo, "Listen, don't be a stranger. The kid is yours too. Just don't stress her out too much, alright? She may act tough, Damon, but she really does need you."

He nodded his head and watched her leave only to see Stefan walk in, "Hey, how is she?"

"Well besides the fact that she kicked me out of the house by throwing a stake at me, Ruby is fine and so is the baby. They are resting comfortably at the moment. Don't go waking her up. Oh and if you think the picture is amazing, wait'll you see the DVD." Stefan informed him with a slight grin and tossed the square plastic case at his older brother who caught it effortlessly.

In the blink of an eye, Damon was sitting down on the couch watching the DVD. A loud strong thumping sound filled the air seemingly echoing through the house and he was just amazed. The pregnant blonde stirred in her sleep for a moment before relaxing comfortably again her even breathing signifying that she was fast asleep. The brunette was standing beside the bed staring down at the pregnant blonde's ever growing baby bump in amazement. Vampires couldn't procreate and yet Damon had. She rolled her brown eyes knowing that if any vampire could successfully procreate, lord knows it would of been Damon.

Her lips twisted into a smirk as she brushed her palm against the baby bump gently, "We are going to have so much fun together, little Salvatore. Just you wait and see."


End file.
